Apeer-reviewed open-access journa I BioRisk 18:57—91 (2022) ites ; doi: 10.3897/biorisk. 18.7700 RESEARCH ARTICLE & B lO R IS https://biorisk.pensoft.net Potential risk resulting from the influence of static magnetic field upon living organisms. Numerically-simulated effects of the static magnetic field upon carbohydrates Wojciech Ciesielski', Tomasz Girek', Henryk Kotoczek’, Zdzistaw Oszczeda?, Jacek A. Soroka*, Piotr Tomasik? I Institute of Chemistry, Jan Dtugosz University, 42 201 Czestochowa, Poland 2 Institute of Chemistry and Inorganic Technology, Krakow University of Technology, 31155 Krakow, Poland 3 Nantes Nanotechnological Systems, 59 700 Bolestawiec, Poland 4 Scientific Society of Szczecin, 71-481 Szczecin, Poland Corresponding author: Wojciech Ciesielski (w.ciesielski@interia.pl) Academic editor: Josef Settele | Received 24 October 2021 | Accepted 3 April 2022 | Published 6 June 2022 Citation: Ciesielski W, Girek T, Kotoczek H, Oszczeda Z, Soroka JA, Tomasik P (2022) Potential risk resulting from the influence of static magnetic field upon living organisms. Numerically-simulated effects of the static magnetic field upon carbohydrates. BioRisk 18: 57—91. https://doi.org/10.3897/biorisk.18.77001 Abstract Background: Recognising effects of static magnetic field (SMF) of varying flux density on flora and fauna is attempted. For this purpose, the influence of SMF upon molecules of a- and /-D-glucose, a- and f-D- galactose, a- and /-fructopyranoses, a- and /s-fructofuranoses and a- and $-D-xylofuranoses and a and {-D-xylopyranoses is studied. Methods: Computations of the effect of static magnetic field (SMF) of 0.0, 0.1, 1, 10 and 100 AFU (1 AFU > 1000 T) flux density were performed in silico for SMF changes distribution of the electron density in these molecules. Hyper-Chem 8.0 software was used together with the AM1 method for optimisation of the conformation of the molecules of monosaccharides under study. Then polarisability, charge distribution, potential and dipole moment for molecules placed in SMF were calculated involving DFT 3-21G method. Results: Application of SMF induced polarisability of electrons, atoms and dipoles, the latter resulting in eventual re-orientation of the molecules along the applied field of the molecules and the electron density redistribution at particular atoms. Increase in the field strength generated mostly irregular changes of the electron densities at particular atoms of the molecules as well as polarisabilities. Energy of these molecules and their dipole moments also varied with the SMF flux density applied. Conclusions: Saccharides present in the living organisms may participate in the response of the living organ- isms to SMF affecting metabolism of the molecules in the body fluids by fitting molecules to the enzymes. Structural changes of saccharide components of the cell membranes can influence the membrane permeability. Copyright Wojciech Ciesielski et al. This is an open access article distributed under the terms of the Creative Commons Attribution License (CC BY 4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. 58 Wojciech Ciesielski et al. / BioRisk 18: 57—91 (2022) Keywords D-fructose, D-galactose, D-glucose, D-xylose, organisms, static magnetic field Introduction Carbohydrates (mono-, di-, oligo- and polysaccharides) serve several key functions in fauna and flora. Customarily, products of their physical, chemical and biological transformations are also accounted for in this group of compounds. Cellulose, a poly- saccharide, is the most abundant carbohydrate all over the world. It is a structural component of the cell walls of plants including aquatic plants like algae. Green plants, which constitute about half of the living matter on the earth, also contain abundant number of mono-, di- and oligosaccharides. Some of them are found also in animals. Metabolism of those oligo- and lower carbohydrates provides energy and nutrients for the plants (Heldt and Piechulla 2010). In organisms of fauna and their life, the role of carbohydrates is much more com- plex than in plants. They co-build membranes of body cells and microorganisms colo- nising the body, enzymes and elements of genetic code. Carbohydrates are present in systems protecting the cells from oxidative stress and participate in several reactions in the body (Maton et al. 1993; Campbell et al. 2006; Reynolds et al. 2019). Carbohy- drates in various forms are delivered to the organisms as food components. ‘The latter are either physically, chemically or enzymatically transformed (metabolised) or left intact playing the role of fibre. Fibre promotes a proper functioning of the excretory system and, as an adsorbent, removes toxins concentrated in the intestines. All kinds of physical, chemical and biochemical transformations are controlled by several fac- tors, such as conformations of reacting molecules, equilibria, formation of transition molecule — enzyme transition states and mechanisms of the transformations which can be either reversible or irreversible. Their transformation can proceed following either ionic or radical mechanisms (Tomasik 1997; Tomasik 2007a, 2007b; Keung and Me- hta 2015; Churuangsuk et al. 2018). The effect of increasing environmental pollution with a magnetic field (Hamza et al. 2002; Rankovic and Radulovic 2009) and the role of the magnetic field in current and future technologies (Committee to Assess the Current Status and Future Direction of High Magnetic Field Science in the United States, Board on Physics and Astronomy 2013; Bao and Guo 2021; Tang et al. 2021) evokes certain anxiety. Therefore, recently (Ciesielski et al. 2021) we presented a numerically-simulated effect of static magnetic field (SMF) on the structure and behaviour of simple molecules, that is, triplet and singlet oxygen, nitrogen, water, ammonia, carbon dioxide and methane (Ciesielski et al. 2021) and lower alkanols (Ciesielski et al. 2022). The results prompted us to study the effect of that field upon further molecules important in constituting and function- ing organisms of flora and fauna. Effects of the static magnetic field on carbohydrates 39 This paper presents results of numerical computations applied to selected monosaccharides, that is to a and f-D-glucose, a and f-D-galactose, a and 6-fructopyranoses, a- and /-fructofuranoses, a- and f-D-xylopyranoses and a- and {-D-xylofuranoses. They play essential roles in building structure and functioning of organisms of flora and fauna. Numerical computations Molecular structures were drawn using the Fujitsu SCIGRESS 2.0 software (March- and et al. 2014). Their principal symmetry axes were orientated along the x-axis of the Cartesian system. A molecule of saccharide was situated inside of a triaxial elypsoid. The long axis of that ellipsoid was accepted to be the x-axis. The shortest axis quasi- perpendicular to either the pyranose or furanose ring was considered as the z-axis. The y-axis was quasi-parallel to those rings plane. The magnetic field was fixed in the same direction, along the x-axis with the south pole from the left side. Subsequently, involv- ing Gaussian 0.9 software, equipped with the 6-31G** basis (Frisch et al. 2016) ice. equipped with multiple polarization functions (Frisch et al. 1984), the molecules were optimised and all values of bond length, dipole moment, health of formation, bond energy and total energy for the systems were computed. In the next step, the tendency of the static magnetic field (SMF) influence, em- ployed as Arbitrary Field Unit (AFU) (1 AFU > 1000 T), upon optimised molecules was computed with Amsterdam Modelling Suite software (Farberovich and Mazalova 2016; Charistos and Mufioz-Castro 2019) and the NR_LDOTB (non-relativistically orbital momentum L-dot-B) method (Glendening et al. 1987; Carpenter and Wein- hold 1988). Following that step, values of bond length, dipole moment, health of formation equal to the energy of dissociation and charges at the atoms, were calculated using Gaussian 0.9 software equipped with the 6-31G** basis (Frisch et al. 2016). Visualisation of molecules in the coordinate system was performed involving the HyperChem 8.0 software (Froimowitz 1993). Results Numerical simulations were performed for both anomers of D-glucose (Fig. 1) Both anomers of D-galactose (Fig. 2) Both anomers of D-fructopyranoses and both anomers of D-fructofuranoeses (Fig. 3) Both anomers of D-xylopyranoses and both anomers of D-xylofuranoses (Fig. 4) Particular structures contain numbering atoms followed in further discussions. Tables 1-3 provide data illustrating properties of the «- and 8-D-glucose molecules situated along the x-axis of the Cartesian system in SMF of the flux density of 0 to 100 AFU, distribution of charge density and bond lengths in those molecules, respectively. Results of those computations are visualised in Fig. 5. 60 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) ri 24 H 16 B— 16 Be H 18 18 Figure 2. Structure of «- and 6-D-galactose (a and b respectively) and followed by numbering of atoms. Table |. Properties of the «- and 8-D-glucose molecules situated along the x-axis of the Cartesian system in SMF of the flux density of 0 to 100 AFU. Property Anomer Flux density [AFU] 0 0.1 1 10 100 Dipole moment [D] o 8.68 8.69 8.77 8.89 9.06 B 8.34 8.44 9.75 10.12 14.52 Heat of formation [kcal/mole] o -1259.6 -1259.6 -1248.7 -1141.5 -985.8 B -1246.6 -1245.8 -1223.5 -1095.3 -912.6 Corresponding data computed for anomers of D-galactose are presented in Tables 4—6. They are visualised in Fig. 6. Tables 7-9 contain results of analogous computations for anomers of D-fructo- pyranoses and visualisation of those data are visualised in Fig. 7. Effects of the static magnetic field on carbohydrates 61 Figure 3. Structure of «- and $-D-fructopyranoses (a and b respectively) and «- and 8-D-fructofuranoses (c and d respectively) and followed by numbering of atoms. Properties computed for anomers of D-fructofuranoses are given in Tables 7, 10 and 11 and their visualisation can be seen in Fig. 8. Corresponding data for D-xylopyranose anomers are provided in Tables 12—14 and visualisation of those data are presented in Fig. 9. Finally, computations for anomers of D-xylofuranoses are presented in Tables 12, 15 and16. Visualisation of those data is given in Fig. 10. Discussion This study focused on recognising effects of SMF upon metabolism of monosaccha- rides in the organisms of fauna and flora. Particular attention was paid to the effect of SMF of increasing flux density upon the charge density at the atoms being the reaction sites of the selected monosaccharide molecules responsible for initiating the metabolic processes. 62 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) ¢ d Figure 4. Structure of «- and §-D-xylopyranoses (a and b respectively) and «- and 8-D-xylofuranoses (c and d respectively) and followed by numbering of atoms. SMF could perturb the trajectory of bonds forming electrons involving the Lor- entz force. Additionally, the stability of the lone and bonding electron pairs resulting from their oppositely-directed magnetic spins could be reduced. Such kind of electron pairs reside in valence bonds and in non-bonding lone electron pairs of the oxygen atoms. One of the two lone electron pairs of the latter atoms should be particularly sensitive to the effect of SMF. SMF could turn hybridisation of that atom from nearly sp’ to sp® proportionally to an increase in the flux density. That effect would influence the electrostatic interactions through space within the molecules. D-Glucose This aldohexose resides chiefly in the cyclic form of «- and $-pyranose (Fig. 1). The thermodynamically less stable open-chain molecule spontaneously isomerises into one of two anomeric pyranoses (Tomasik 1997; Tomasik 2007a;, 2007b; Keung and Mehta 2015; Churuangsuk et al. 2018). Both anomers of D-glucose, that is, «- and 8-D-glucose are utilied in organisms of flora and fauna as a main source of energy (Domb et al. 2019). They are directly Effects of the static magnetic field on carbohydrates 63 Table 2. Charge density [a.u] at particular atoms of the «- and 8-D-glucose molecules depending on SMF flux density [AFU]. Atom Fluxdensity[AFU] Tendency 0 0.1 1.0 10 100 Cl H1 0.421 0.428 0.430 0.435 0.434 12 0.466 0.442 0.425 0.398 0.375 C2 H3 0.094 0.108 0.126 0.148 0.156 H2 0.138 0.149 0.161 0.172 0.178 C3 V 0.135 0.137 0.129 0.050 0.053 V 0.108 0.108 0.079 0.050 0.093 C4 V 0.176 0.179 0.181 0.153 0.164 Ll 0.192 0.192 0.187 0.166 0.163 C5 IL 0.121 0.121 0.124 0.076 0.067 IL 0.102 0.110 0.096 0.058 0.034 C6 H3 0.004 0.010 0.036 0.371 0.427 H 0.009 0.027 0.139 0.374 0.460 O7 TH -0.639 -0.636 -0.632 -0.620 -0.628 H2 -0.631 -0.620 -0.610 -0.598 -0.017 O8 12 -0.697 -0.706 -0.715 -0.734 -0.736 H2 -0.727 -0.708 -0.702 -0.696 -0.688 O9 TH -0.706 -0.708 -0.708 -0.689 -0.683 H -0.752 -0.750 -0.740 -0.716 -0.696 O10 TH -0.752 -0.745 -0.721 -0.475 -0.551 H2 -0.745 -0.712 -0.580 -0.489 -0.634 Oll Vv -0.744 -0.741 -0.738 -0.724 -0.740 Vv -0.747 -0.740 -0.735 -0.728 -0.753 O12 V -0.711 -0.715 -0.716 -0.669 -0.651 H1 -0.708 -0.707 -0.702 -0.659 -0.600 H13 V 0.174 0.173 0.172 0.184 0.187 V 0.150 0.147 0.155 0.169 0.172 H14 L 0.182 0.178 0.175 0.174 0.175 V 0.192 0.191 0.161 0.201 0.201 H15 IH 0.200 0.201 0.204 0.241 0.240 V 0.155 0.153 0.164 0.172 0.134 H16 V 0.196 0.195 0.194 0.198 0.191 V 0.207 0.207 0.207 0.211 0.205 H17 IH 0.186 0.185 0.186 0.228 0.230 H1 0.161 0.162 0.179 0.214 0.221 H18 L3 0.155 0.130 0.075 -0.479 -0.493 L3 0.156 0.093 -0.087 -0.488 -0.434 H19 TH 0.186 0.183 0.185 0.256 0.278 H2 0.186 0.183 0.197 0.257 0.513 H20 H1 0.406 0.409 0.412 0.438 0.439 V 0.415 0.410 0.408 0.415 0.408 H21 Vv 0.395 0.396 0.393 0.393 0.396 LI 0.422 0.420 0.413 0.407 0.391 H22 L3 0.405 0.396 0.370 0.120 0.087 L2 0.423 0.395 0.285 0.187 0.133 H23 V 0.417 0.417 0.416 0.422 0.433 V 0.420 0.420 0.418 0.424 0.438 H24 H2 0.395 0.407 0.421 0.502 0.523 H2 0.397 0.418 0.451 0.500 0.513 *Data in normal font and in italics are for «- and 8-anomers, respectively. Data given in bold are related to the effects at atoms which could be interpreted in details as not perturbed by a free rotation. Notation: H - high, L - low, IH and IL- irregular high and irregular low changes, respectively and V — totally irregular changes of the values. Figures following symbol or L characterise intensity of the change: 1 —weak, 2 — moderate, 3 — very strong. 64 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) Table 3. Bond lengths [A] in the a- and 6-D-glucose molecules depending on the applied SMF flux density [AFU]*. Bond Flux density [AFU] Tendency 0 0.1 1 10 100 C1-C2 H1 1.530 1.536 1.554 1.579 1.587 Hl 1.528 1.533 1.534 1.539 1.552 C1-08 Ll 1.413 1.413 1.408 1.389 1.394 Ll 1.390 1,389 1,387 1,382 1.382 O8-H20 H1 0.972 1.011 1.048 1.041 1.045 V 0.972 1.058 1.020 1.062 1,028 C1-H13 H1 1.099 1.117 1.125 1.121 1.126 H1 1.100 1,194 1.169 1.164 1.156 C2-C3 H1 1.528 1.530 1.533 1.553 1.561 H1 1.526 1.532 1.545 1.552 1.547 C2-09 H1 1.412 1.411 1.413 1.427 1.427 H1 1,412 1,416 1.417 1,424 1.431 O9-H21 V 0.972 1.007 1.004 1.004 0.993 V 0.972 0.989 0.983 0.955 0.969 C2-H14 H1 1.099 1.147 1.153 1.155 1.149 H1 1.099 1.187 1.170 1.152 1.155 C3-C4 Vv 1.527 1.518 1.514 1.525 1.523 V 1.527 1.514 1.517 1.530 1.534 C3-010 Vv 1.412 1.416 1.423 1.381 1.397 Vv 1.412 1.419 1.3934 1.378 1.194 O10-H22 H3 0.972 1.198 1.389 3.084 3.685 H3 0.972 1.378 1.979 2.886 3.990 C3-H15 H1 1.099 1.115 1.132 1.127 1.134 H1 1.099 1,132 1.116 1,148 1.125 C4-C5 Vv 1.533 1.529 1.531 1.529 1.525 Vv 1.532 1.530 1,527 1,533 1.538 C4-O11 H1 1.412 1.422 1.434 1.461 1.476 H1 1,412 1.427 1,442 1.455 1.461 O11-H23 V 0.972 0.968 0.972 0.964 0.964 Vv 0.972 0.969 0.957 0.977 0.970 C4-H16 H2 1.099 1.161 1.169 1.176 1.171 H2 1.099 1.187 1,168 1,140 1.153 C5-C6 H1 1.528 1.531 1.540 1.556 1.570 H1 1,528 1,532 1,538 1.553 1.559 C6-O12 IL 1.412 1.392 1.368 1.292 1.298 IL 1.412 L375 1,328 1,287 1.309 O12-H24 H 0.972 0.995 1.011 1.050 1.058 H 0.972 1,026 1.048 1.050 1.061 C6-H18 H2 1.099 1.148 1.150 1.168 1.169 V 1.099 1.184 1.204 1175 1.189 Co-H19 H3 1.099 1.262 1.444 2.675 3.259 H3 1.099 1.410 LI7L 2.656 3.742 C5-O7 V 1.433 1.431 1.429 1.429 1.437 V 1.434 1.430 1,430 1,435 1.467 O7-Cl1 Ll 1.433 1.414 1.392 1.387 1.375 V 1,432 1,402 1.3942 1.400 1,403 ‘See Table 2 for notation. Effects of the static magnetic field on carbohydrates 65 Figure 5. Simplified visualisation of the effect of SMF upon conformation and bond length of «-D- and 8-D-glucose anomers (a—c and d-f respectively), situated in the Cartesian system. 66 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) Table 4. Properties of the «- and 8-D-galactose molecules situated along the x-axis of the Cartesian sys- tem in SMF of the flux density of 0 to 100 AFU. Property Anomer Flux density [AFU] 0 0.1 1 10 100 Dipole moment [D] o 8.63 8.72 8.83 8.93 9.18 ) 8.66 8.72 8.88 8.98 9.32 Heat of formation [kcal/mole] o -1286.3 -1285.2 -1267.4 -1206.5 -1128.4 8 -1252.3 -1251.2 -1247.4 -1198.7 -1111.3 metabolised in the body. In human organisms, that energy is generated chiefly from glycogen stored in the liver. Under specific cases, D-glucose is delivered into organ- isms as a component of food, for instance, a spice and supplement of diet injected as an additional source of energy (World Health Organization 2019). D-Glucose is metabolised in enzymatic processes. The first step of that process involves its esterifica- tion with adenosine-triphosphate (ATP) at the C6-OH group (Heinrich et al. 2014). Within the Entner-Doudoroff pathway operating in Gram-negative bacteria, certain Gram-positive bacteria and archaea begin at the same reaction site engaging the Cl atom (Conway 1992). One of the important enzymatic reactions of D-glucose, called the Maillard reac- tion, is known as the enzymatic browning reaction. In the reaction of D-glucose with lysine and arginine, residues of the protein pentosidine are formed (Sell and Monnier 1989). Pentosidine is formed most readily from pentoses, but glucose, fructose and other saccharides may also react in such a manner. Performed computations showed that, based on the criterion of heat of formation, the «-D-anomer was slightly more stable than the 8-D-anomer (Table 1). The stabil- ity of both anomers decreased unevenly against the applied SMF flux density. The 8-D-anomer reacted more strongly to SME It was also associated with a significantly stronger increase in dipole moment. These trends fitted results performed with density functional/ab initio computation in silico. The same computations for both anomers of D-glucose in water pointed to the «-D-anomer as more stable than the 8B-D-anomer (Facundo Ruiz et al. 2005). However, electrochemical oxidation of the «-D-anomer glucose and 8-D-anomer on the anode surface showed that the 8-D-anomer was much more reactive (Largeaud et al. 1995). The charge density at particular atoms of both anomers varied irregularly with an increase in the flux density (Table 2). An increase in the SMF flux density produced a more remarkable decrease in the electron density at the 1,2,4,5,6,7,11,12,15 and 20 atoms of the B-anomer than at the same atoms of the «-anomer. Extremely strong, but an opposite effect was noted at the C2 and H21 atoms. Both atoms were bound to one another and the C2 atom was in the vicinity to the endocyclic O7 atom. Thus, observed effects could result from electrostatic interactions through space involving a partially weakened lone electron pair of the oxygen atom. An increase in the electron density produced by SMF was observed at C18 (atom Cl, 8-anomer), C48, C5, O8« and H14« atoms, whereas the electron density remarkably decreased at Cla, C2, O7«, Effects of the static magnetic field on carbohydrates 67 Table 5. Charge density [a.u] at particular atoms of the «- and 8-D-glucose molecules depending on SMF flux density [AFU]. Atom Flux density [AFU] Tendency 0 0.1 1.0 10 100 Cl V 0.447 0.456 0.452 0.439 0.399 V 0.448 0.436 0.426 0.431 0.398 C2 H1 0.112 0.113 0.132 0.148 0.203 TH 0.191 0.197 0.200 0.185 0.210 C3 IL 0.102 0.131 0.086 0.040 0.099 Ll 0.112 0.111 0.090 0.045 0.077 C4 IH 0.086 0.094 0.108 0.114 0.105 V 0.118 0.125 0.128 0.128 0.107 C5 L2 0.129 0.129 0.027 -0.044 -0.112 IL 0.107 0.112 0.080 0.002 -0.069 C6 H2 -0.038 -0.043 0.212 0.310 0.483 H2 -0.040 -0.062 0.001 0.249 0.476 O7 V -0.641 -0.641 -0.645 -0.637 -0.641 IL -0.629 -0.626 -0.622 -0.612 -0.623 O8 IL -0.714 -0.734 -0.749 -0.749 -0.745 H1 -0.698 -0.688 -0.669 -0.668 -0.646 O9 Vv -0.747 -0.746 -0.745 -0.742 -0.772 Vv -0.728 -0.721 -0.713 -0.700 -0.733 010 V -0.747 -0.758 -0.607 -0.502 -0.712 Vv -0.719 -0.706 -0.665 -0.483 -0.692 O11 H1 -0.777 -0.769 -0.731 -0.679 -0.608 H1 -0.690 -0.685 -0.667 -0.660 -0.617 O12 H -0.758 -0.727 -0.677 -0.619 -0.534 H -0.724 -0.704 -0.674 -0.628 0.551 H13 V 0.183 0.184 0.184 0.195 0.181 Vv 0.156 0.146 0.144 0.150 0.163 H14 V 0.190 0.181 0.182 0.190 0.183 V 0.220 0.219 0.218 0.228 0.210 H15 V 0.196 0.202 0.217 0.233 0.150 V 0.167 0.167 0.170 0.183 0.110 H16 V 0.189 0.195 0.205 0.214 0.200 H1 0.185 0.186 0.192 0.205 0.209 H17 TH 0.204 0.233 0.302 0.354 0.353 H1 0.174 0.179 0.195 0.236 0.267 H18 H1 0.205 0.204 0.239 0.283 0.301 TH 0.182 0.166 0.169 0.214 0.283 H19 12 0.181 0.093 -0.277 -0.496 -0.315 L2 0.163 0.158 0.040 -0.349 -0.376 H20 H1 0.431 0.436 0.443 0.451 0.457 V 0.395 0.396 0.394 0.408 0.388 H21 V 0.435 0.433 0.422 0.423 0.434 H1 0.411 0.412 0.412 0.413 0.420 H22 IL 0.445 0.449 0.443 0.209 0.078 IL 0.394 0.379 0.339 0.179 0.105 H23 Ll 0.461 0.446 0.414 0.384 0.325 Ll 0.398 0.394 0.382 0.374 0.339 H24 H1 0.425 0.438 0.455 0.480 0.487 H1 0.409 0.411 0.427 0.472 0.524 See Table 2 for notation. 68 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) Table 6. Bond lengths [A] in the «- and 8-D-galactose molecules depending on the applied SMF flux density [AFU]*. Bond Tendency Flux density [AFU] 0 0.1 1 10 100 C1-C2 V 1.5120 1.528 1.551 1.542 1.551 V 1.540 1,543 1.560 1.556 1.551 C1-O8 V 1.404 1.412 1.110 1.411 1.401 V 1.430 1,421 1.400 1.388 1.366 O8-H20 V 0.978 0.974 0.962 0.974 0.966 IH 0.960 1.011 1.071 1,026 1.096 C1-H13 V 1.100 1.141 1.103 1.149 1.116 V 1.090 1.179 1.168 1.172 1.092 C2-C3 Vv 1.515 1.497 1.504 1.576 1.536 V 1.537 1.520 1.505 1.510 1,543 C2-09 V 1.408 1.390 1.386 1.390 1.410 IL 1.430 1,416 1.394 1.386 1,424 O9-H21 Vv 0.979 1.003 0.962 0.991 0.955 V 0.960 1.013 1.014 0.998 0.972 C2-H14 Vv 1.100 1.189 1.171 1.212 1.166 TH 1.090 1.137 1.171 1.180 1.159 C3-C4 Vv 1.512 1.509 1.515 1.519 1.513 Vv 1.537 1,532 1.522 1.532 1.528 C3-0O10 V 1.407 1.490 1.380 1.364 1.381 Ll 1.430 1,429 1,427 1.374 1.370 O10-H22 H3 0.922 1.345 2.062 2.947 4.432 H3 0.960 1.191 1.439 2.279 3.963 C3-H15 V 1.100 1.145 1.140 1.143 1.154 TH 1.090 1.117 1.139 1.121 1,144 C4-C5 Ll 1.539 1.525 1.521 1.512 1.509 IL 1.540 1,535 1.534 1,532 1,533 C4-O11 Vv 1.412 1.432 1.153 1.158 1.475 H1 1.430 1,433 1,445 1,452 1.467 O11-H23 V 0.982 0.932 1.005 0.932 0.972 V 0.960 0.938 0.995 0.927 0.960 C4-H16 V 1.101 1.137 1.121 1.141 1.135 TH 1.090 L111 1.130 1.117 1.138 C5-C6 IL 1.534 1.489 1.448 1.437 1.479 Vv 1.540 1.516 1.439 1.477 1.529 C6-O12 V 1.100 1.543 1.099 1.210 1.123 V 1.090 1,167 LA27 1,182 1,132 O12-H24 V 0.975 1.013 0.988 1.033 1.000 V 0.960 1.021 1,031 1.080 1.081 C6-H18 L2 1.418 1.404 1.380 1.346 1.339 12 1.430 1.417 1.374 1.314 1.274 Co-H19 H3 1.100 1.108 2.360 3.401 5.114 H3 1.090 1.201 1.659 2.450 4.717 C5-H17 V 1.100 1.227 1.222 1.260 1.235 Vv 1.090 1.158 1.177 1,434 1.152 C5-O7 Vv 1.432 1.437 1.440 1.439 1.432 Vv 1.433 1.434 1.437 1.434 1.429 O7-Cl V 1.431 1.420 1.419 1.428 1.430 Vv 1,433 1.430 1.427 1.442 1.456 ‘See Table 2 for notation. Effects of the static magnetic field on carbohydrates 69 4 Figure 6. Simplified visualisation of the effect of SMF upon conformation and bond length of «-D- and 8-D-galactose anomers (a=c and d-f respectively), situated in the Cartesian system. (see Fig. 2 for notation). 70 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) Table 7. Properties of the «- and $-D-fructopyranose and corresponding «- and §-D-fructofuranose molecules situated along the x-axis of the Cartesian system in SMF of the flux density of 0 to 100 AFU’. Property Anomer Flux density [AFU] 0 0.1 1 10 100 Dipole moment [D] a-D-Frup 3.63 3.67 3.76 3.93 4.24 6-D-Frup 3.60 3.61 3.69 3.86 4.16 a-D-Fruf 3.68 3.69 3.87 3.92 4.16 6-D-Fruf 3.66 3.71 3.85 3.90 4.09 Heat of formation [kcal/mole] a-D-Frup -1193.2 -1190.4 -1153.8 -1140.6 -1096.5 6-D-Frup -1205.5 -1203.2 -1199.9 -1156.7 -1026.5 a-D-Fruf -1255.6 -1253.5 -1231.5 -1231.5 -1201.8 6-D-Fruf -1245.6 -1243.5 -1238.6 -1221.4 -1198.5 *Upper and lower values (in italics) are for «- and $-isomers, respectively. O78, O88, O9, O10 and H15a atoms. Small and irregular changes of electron density could be observed at C3, C4«, O11, H13, H148, H158 and H16 atoms. Remarkable changes were noted at the C1, C5 and C2 atoms. In fact, in a real molecule, all hydrogen atoms of the OH groups changed their positions by free rotation because of the practically identical energy between particular rotamers of those groups. This problem was well illustrated by the results of computa- tion for the twin hydrogen H18 and H19 atoms. Due to accepted computation meth- odology, the free rotation around the C5-C6 bond was eliminated. In consequence, the H18 atom holds a considerable negative charge, whereas the H19 atom took increased positive charge density. As a result, results of the computations for particular rotamers could not be interpreted in detail in this case as well as in the cases of subsequently discussed carbohydrates. For D-glucose, these restrictions were also valid for the H20, H21, H22, H23, H24 and O12 atoms. Results of detailed analysis of the remaining O7, O8, O9, O10, O11, C1, C2, C3, C4, C5, C6, H13, H14, H15 and H16 atoms are identified in Table 2. Generally, atoms of the pyranose skeleton were moderately sensitive to SME, al- though increasing SMF flux density considerably decreased basicity of the ring O5 atom in the B-anomer. The O and H atoms were the most and least sensitive, respec- tively, to the effect of SME In the group bound to the C3 atom perpendicularly to the field, an increase in the flux density decreased the negative charge density at the O10 atom and the positive charge density at the H22 atom. It suggested a decrease in the acidity of that group. In the quasi-parallel orientated O8-H20 group, SMF evoked the opposite effect. Thus, the accepted orientation of the molecule under consideration ap- peared very essential. One of the biochemically most important OH group at the C6 atom turned more acidic and that effect could noticeably influence the biochemistry of D-glucose. Review of Table 2 also identified that increased positive charge density at the Cl in the «-anomer favoured attacks of various Lewis bases at this position. Such reac- tions were also important from the biochemical point of view. Simultaneously, the reactivity of the B-anomer involving this position was partly inhibited as the positive Effects of the static magnetic field on carbohydrates 71 Table 8. Charge density [a.u] at particular atoms of the «- and 8-D-glucose molecules depending on SMF flux density [AFU]. Atom Flux density [AFU] Tendency 0 0.1 1.0 10 100 C1 H3 -0.049 -0.068 0.048 0.147 0.275 H3 -0.027 -0.036 -0.018 0.131 0.493 C2 H2 0.118 0.159 0.166 0.169 0.173 L2 0.103 0.098 0.098 0.062 -0.027 C3 V 0.098 0.051 0.052 0.050 0.052 V 0.130 0.145 0.146 0.131 0.089 C4 IL 0.160 0.084 0.076 0.071 0.096 V 0.175 0.185 0.144 0.117 0.179 C5 Vv 0.541 0.576 0.552 0.552 0.487 Vv 0.522 0.547 0.550 0.525 0.481 C6 IL 0.015 -0.068 -0.044 -0.046 -0.002 H1 -0.025 -0.021 0.015 0.027 0.032 O7 Vv -0.578 -0.578 -0.570 -0.561 -0.540 Vv -0.598 -0.598 -0.607 -0.586 -0.568 O8 L -0.699 -0.709 -0.733 -0.741 -0.758 IH -0.705 -0.701 -0.700 -0.691 -0.661 O9 H1 -0.751 -0.709 -0.688 -0.688 -0.683 H1 -0.748 -0.743 -0.715 -0.693 -0.668 010 Vv -0.734 -0.463 -0.453 -0.472 -0.586 IH -0.752 -0.709 -0.563 -0.434 -0.572 O11 V -0.676 -0.635 -0.631 -0.643 -0.639 Vv -0.728 -0.744 -0.751 -0.740 -0.754 O12 H2 -0.691 -0.660 -0.662 -0.657 -0.540 IL -0.694 -0.697 -0.690 -0.713 -0.725 H13 H2 0.180 0.210 0.245 0.260 0.289 V 0.212 0.210 0.202 0.222 0.272 H14 LI 0.208 0.171 -0.048 -0.175 -0.260 IL 0.192 0.194 0.188 -0.011 -0.329 H15 H1 0.171 0.178 0.196 0.201 0.206 TH 0.169 0.161 0.162 0.184 0.212 H16 V 0.166 0.194 0.194 0.193 0.191 V 0.176 0.172 0.171 0.185 0.187 H17 V 0.228 0.234 0.235 0.240 0.229 TH 0.239 0.234 0.248 0.261 0.281 H18 V 0.165 0.157 0.149 0.146 0.179 V 0.121 0.094 0.089 0.133 0.174 H19 V 0.159 0.200 0.202 0.212 0.142 V 0.198 0.196 0.198 0.184 0.180 H20 H2 0.360 0.422 0.434 0.446 0.467 V 0.413 0.413 0.408 0.414 0.424 H21 V 0.386 0.413 0.411 0.423 0.420 V 0.415 0.421 0.415 0.417 0.428 H22 V 0.418 0.116 0.099 0.110 0.130 L2 0.405 0.359 0.195 0.045 0.024 H23 Vv 0.416 0.316 0.358 0.372 0.387 V 0.407 0.412 0.402 0.406 0.430 H24 V 0.390 0.363 0.372 0.372 0.375 H2 0.198 0.408 0.411 0.418 0.427 aSee Table 2 for notation. 72 Wojciech Ciesielski et al. / BioRisk 18: 57—91 (2022) Z Table 9. Bond lengths [A] in the «- and 8-D-fructopyranose molecules depending on the applied SMF flux density [AFU]*. Bond Flux density [AFU] Tendency 0 0.1 1 10 100 C1-C2 Vv 1.540 1.575 1.561 1.563 1.571 Vv 1.540 1,537 1.545 1.530 1.516 C1-H13 H3 1.090 1.562 2.053 2.481 3.678 H3 1.090 1.240 1,323 1.936 3.435 C1-H14 V 1.090 1.091 1.145 1.006 1.172 V 1.090 1.102 1.116 1.126 1.100 C2-C3 Vv 1.537 1.559 1.544 1.568 1.519 Vv 1.537 1.531 1.546 1.544 1.541 C2-08 H1 1.430 1.433 1.437 1.437 1.439 H1 1.430 1.435 1.435 1.445 1.473 O8-H20 V 0.960 1.026 0.968 1.026 1.017 V 0.960 0.952 1.050 0.985 1.030 C2-H15 V 1.090 1.252 1.190 1.217 1.234 V 1.090 1.217 1.178 1.215 1.198 C3-C4 Vv 1.537 1.562 1.570 1.568 1.566 IH 1.537 1.546 1.564 1.571 1.524 C3-O10 Vv 1.430 1.470 1.415 1.394 1.389 IL 1.430 1.396 1.370 1.371 1.368 O10-H21 V 0.960 0.986 0.916 1.017 0.907 V 0.960 0.971 0.929 0.954 0.993 C3-H16 V 1.090 1.193 1.137 1.202 1.173 V 1.090 1,127 1.113 1,122 1.1103 C4-C5 H1 1.540 1.621 1.622 1.627 1.628 Hl 1.540 1.547 1.560 L575 1.598 C4-O11 V 1.430 1.547 1.527 1.522 1.517 V 1.430 1.447 1,446 1,427 1,444 O11-H22 H3 0.960 2.268 2.928 3.341 3.781 H3 0.960 1,333 1.972 2.847 4.49] C4-H17 V 1.090 1.137 1.110 1.137 1.116 V 1.090 1.099 1.410 1.087 1.083 C5-C6 V 1.540 1.638 1.596 1.580 1.526 TH 1.540 1.516 1.560 1.567 1.570 C5-09 IL 1.430 1.374 1.364 1.354 1.356 V 1.090 1.430 1.458 1.456 1,445 O9-H23 V 0.960 1.035 0.910 1.016 0.897 V 0.960 1.013 0.913 0.982 1.022 C6-O12 V 1.430 1.556 1.471 1.435 1.423 IL 1.430 1.413 1.378 1.388 L379: O12-H24 V 0.960 0.963 0.932 0.974 0.928 Vv 0.960 0.906 0.988 0.967 0.912 C6-H18 V 0.960 1.101 1.119 1.080 1.111 IL 1.960 1.134 1.083 1,163 1,167 Co-H19 H2 1.090 1.128 1.154 1.157 1.569 V 1.090 1.184 1.205 1.107 1.170 C5-O7 Vv 1.433 1.387 1.397 1.393 1.416 V 1,432 1.417 1.392 1,402 1.400 O7-Cl TH 1.433 1.467 1.477 1.485 1.462 Vv 1,433 1.454 1.481 1.470 1.470 ‘See Table 2 for notation. Effects of the static magnetic field on carbohydrates hs: Figure 7. Simplified visualisation of the effect of SMF upon conformation and bond length of «-D- and $-D- fructopyranose anomers (a=—c and d-f respectively), situated in the Cartesian system (see Fig. 2 for notation). 74 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) Table 10. Charge density [a.u] at particular atoms of the «- and 8-D-glucose molecules depending on SMF flux density [AFU]. Atom Flux density [AFU] Tendency 0 0.1 1.0 10 100 Cl IL 0.521 0.528 0.523 0.499 0.464 H2 0.508 0.561 0.581 0.617 0.714 C2 L2 0.020 0.002 -0.012 -0.022 -0.037 IL 0.155 0.118 0.080 0.058 0.059 C3 V 0.129 0.129 0.124 0.121 0.189 IL 0.116 0.104 0.111 0.086 -0.005 C4 H1 0.115 0.122 0.128 0.130 0.140 Ll 0.092 0.080 0.079 0.071 0.032 C5 TH 0.097 0.086 0.109 0.206 0.405 12 0.034 0.015 -0.002 -0.023 -0.143 C6 IL 0.035 0.035 0.027 -0.016 -0.063 IL -0.006 -0.019 -0.038 -0.023 -0.038 O7 Vv -0.589 -0.597 -0.604 -0.511 -0.620 V -0.625 -0.634 -0.676 -0.658 -0.642 O8 H1 -0.656 -0.639 -0.628 -0.625 -0.560 V -0.711 -0.718 -0.665 -0.686 -0.469 O9 IL -0.712 -0.696 -0.670 -0.641 -0.680 H2 -0.741 -0.714 -0.686 -0.588 -0.380 O10 IH -0.711 -0.691 -0.677 -0.670 -0.680 TH -0.734 -0.712 -0.714 -0.699 -0.667 Oll H1 -0.674 -0.641 -0.620 -0.605 -0.580 H1 -0.700 -0.702 -0.690 -0.675 -0.607 O12 H2 -0.696 -0.682 -0.644 -0.500 -0.359 IH -0.743 -0.724 -0.709 -0.722 -0.699 H13 H1 0.217 0.219 0.222 0.228 0.245 IL 0.235 0.228 0.205 0.221 -0.218 H14 H1 0.180 0.182 0.184 0.188 0.189 TH 0.184 0.182 0.192 0.198 0.259 H15 H1 0.205 0.205 0.207 0.212 0.225 V 0.196 0.202 0.187 0.200 0.202 H16 H1 0.167 0.170 0.178 0.196 0.244 Ne 0.173 0.164 0.139 0.076 0.190 H17 L2 0.104 0.064 -0.004 -0.148 -0.470 H1 0.182 0.183 0.196 0.200 0.212 H18 VI 0.169 0.161 0.159 0.175 0.248 H 0.173 0.176 0.202 0.194 0.217 H19 V 0.148 0.142 0.143 0.154 0.171 V 0.173 0.159 0.174 0.162 0.179 H20 Vv 0.365 0.364 0.366 0.374 0.388 V 0.415 0.433 0.451 0.408 0.124 H21 H2 0.389 0.395 0.402 0.419 0.454 V 0.397 0.405 0.396 0.416 0.419 H22 L2 0.387 0.373 0.355 0.341 0.295 L2 0.401 0.394 0.385 0.304 0.244 H23 V 0.403 0.400 0.397 0.398 0.407 Vv 0.414 0.410 0.398 0.397 0.401 H24 L3 0.388 0.373 0.335 0.198 0.005 V 0.412 0.411 0.404 0.410 0.416 ‘See Table 2 for notation. Effects of the static magnetic field on carbohydrates vie) Z Table 11. Bond lengths [A] in the «- and 8-D-fructofuranose molecules depending on the applied SMF flux density [AFU]*. Bond Flux density [AFU] tendency 0 0.1 1 10 100 C1-C2 H1 1.540 1.549 1.559 1.570 1.592 H3 1.539 1.624 1.847 2.084 2.422 C1-O8 V 1.413 1.408 1.406 1.406 1.409 V 1.430 1.365 1.273 1.304 1.225 O8-H20 Hl 0.960 0.955 0.970 0.978 0.985 H3 0.960 0.994 1,155 1,183 1.783 C1-C5 Ll 1.535 1.521 1.511 1.502 1.495 IL 1.540 1.527 1.509 1.473 1.485 C5-Ol1 IH 1.412 1.389 1.586 1.376 1.848 Ve 1.430 1.439 1,442 1.421 1.370 O11-H21 Vv 0.960 0.960 0.970 0.978 0.995 V 0.960 0.992 0.982 0.961 1.001 C5-H16 V 1.091 1.151 1.150 1.121 1.112 V 1.090 1,145 1,132 1,128 1,132 C5-H17 H3 1.091 1.365 1.586 1.936 2.922 V 1.090 1,337 1,242 1.358 1,255 C2-C3 Vv 1.523 1.514 1.513 1.519 1.541 IL 1.539 1.536 1.497 1.477 1.522 C2-09 V 1.412 1.422 1.427 1.426 1.395 Vv 1,430 1.398 1.327 1.298 1.177 O9-H22 H3 0.959 1.173 1.322 1.487 2.036 H3 0.960 1.063 1.069 1,322 3.213 C2-H13 H1 1.092 1.109 1.120 1.124 1.153 V 1.090 1,172 1,142 1,131 1.153 C3-C4 IL 1.524 1.517 1.514 1.511 1.515 H1 1.540 1.544 1.596 1.601 1.610 C3-0O10 IL 1.412 1.398 1.390 1.386 1.399 H2 1.430 1.945 1.533 1.577 1.614 O10-H23 V 0.960 1.000 1.000 0.983 0.946 Vv 0.960 0.971 0.986 1.001 0.995 C3-H14 H1 1.091 1.103 1.131 1.146 1.178 V 1.090 1,453 1.119 1,132 1,106 C4-O7 H1 1.414 1.416 1.425 1.441 1.465 V 1,431 1.421 1.420 1.420 1.432 C4-C6 IH 1.531 1.532 1.536 1.540 1.5397 Vv 1.540 1.558 1,539 1.561 1.557 C4-H15 H1 1.092 1.142 1.166 1.172 1.198 V 1.090 1,207 1.079 1.069 1.036 Co6-O12 IL 1.411 1.417 1.410 1.391 1.360 V 1.430 1.450 1.580 1.499 1.505 O12-H24 H3 0.960 1.166 1.378 1.902 3.080 Vv 0.960 0.990 0.961 0.927 0.958 Co-H18 V 1.090 1.134 1.132 1.122 1.122 V 1.090 1,273 1.143 1,233 1,201 C6-H19 H2 1.098 1.190 1.246 L257 1.290 IH 1.090 1,139 1.147 1,139 1.155 O7-Cl Ll 1.421 1.420 1.420 1.417 1.409 vil 1,431 1,457 1.437 1,402 1.412 ‘See Table 2 for notation. 76 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) Figure 8. Simplified visualisation of the effect of SMF upon conformation and bond length of «-D- and $-D- fructofuranose anomers (a=—c and d-f respectively), situated in the Cartesian system (see Fig. 2 for notation). Effects of the static magnetic field on carbohydrates el, Table 12. Properties of the «- and 8-D-xylose molecules situated along the x-axis of the Cartesian system in SMF of the flux density of 0 to 100 AFU*. Property Anomer Flux density [AFU] 0 0.1 1 10 100 Dipole moment [D] a-D-Xylp 4.22 4.24 4.31 4.67 4.73 8-D-Xylp 1.22 1.23 1.29 1.37 1.47 a-D-Xylf 4.85 4.89 4.94. 5 5.69 8-D-Xylf 4.87 4.89 4.95 5.01 5.19 Heat of formation [kcal/mole] a-D-Xylp -1143.2 -1127.4 -1089.6 -1061.2 -1005.4 8-D-Xylp -1154.2 1147.3 -1110.3 -1089.5 -1021.8 a-D-Xylf -1076.2 —1075.4 -1069.4 -1041.3 -995.6 8-D-Xylf -1051.2 -1049.5 -1036.4 -1004.4 952.3 *Upper and lower values (in italics) are for «- and $-isomers, respectively. charge density at this atom declined under the influence of SMF. The SMF induced an increase in the positive charge density at the C6 atom. It was non-beneficial for enzy- matic processes starting from esterification with adenosine-triphosphate (ATP) at C6- O24 and the functioning of the Entner-Doudorff metabolic pathway (Conway 1992). An insight into the effect of SMF upon the length of bonds in the molecules of both anomers (Table 3) suggested that these changes resulted from a deformation of the molecules and their deviation from the initially-established location of the mol- ecules along the x-axis. Tendencies of the changes of computed values with an increase in the flux density (Table 3) pointed to a uniform increase in the length of the valence bonds, that is, to weakening their energy. Simultaneously, strongly polarised bonds, with participation of the Cl atom, were regularly shortened, whereas the length of the C3-C4, C3-O10, C3-C5 and C5-O7 bonds varied irregularly. Generally, in the 28 analysed bonds in each anomer, 16 bonds were elongated, four bonds were shortened and the length of eight bonds varied irregularly against increased SMF flux density. These results supported the hypothesis on the weakening of the bonding electron pair. The SMF generated shortening of the C1-O8 bond and elongation of the O8-H20 bond seemed to be the most important. This effect implied the increased susceptibil- ity of the hemi-acetal ring to its opening. Hence, SMF should favour a shift of the mutarotation equilibrium towards the open chain form of D-glucose. This fact could promote the Maillard reaction which proceeds on the open chain forms of saccharides (Grandhee and Monnier 1991). Visualisation of the data from Table 3 (Fig. 5) also includes non-analysable bonds. The conformation of particular anomers is presented in the form of superposition of the molecules without SMF (green colour) and molecules in the SMF of 100 AFU (blue colour). The oxygen atoms are marked red. Structures a and d are given as the projection along the y-axis, whereas the 6 and e structures are projections along the z-axis. Structures c and fare superpositions of the same molecules demonstrating the SMF flux density-dependent change in the bond lengths in the molecules under con- sideration. Structures in Fig. 5 demonstrate a small effect of SMF upon the conforma- tion of both anomers and a significant effect upon the bond lengths of some peripheral 78 Wojciech Ciesielski et al. / BioRisk 18: 57—91 (2022) Table 13. Charge density [a.u] at particular atoms of the «- and 8-D-glucose molecules depending on SMF flux density [AFU]. Atom Flux density [AFU] Tendency 0 0.1 1.0 10 100 Cl H2 0.388 0.400 0.424 0.450 0.460 V 0.474 0.476 0.460 0.478 0.492 C2 12 0.093 0.085 0.035 -0.039 -0.059 12 0.087 0.058 0.057 -0.032 -0.055 C3 V 0.191 0.191 0.130 0.142 0.134 V 0.119 0.117 0.108 0.110 0.109 C4 TH 0.142 0.145 0.161 0.172 0.167 TH 0.163 0.179 0.195 0.215 0.196 C5 H2 -0.042 -0.038 -0.029 0.010 0.125 H2 -0.059 -0.048 -0.058 -0.040 0.066 O6 V -0.602 -0.603 -0.568 -0.560 -0.605 Vv -0.590 -0.590 -0.585 -0.569 -0.577 O7 Vv -0.695 -0.697 -0.749 -0.682 -0.704 V -0.683 -0.665 -0.661 -0.653 -0.674 O8 H2 -0.735 -0.730 -0.649 -0.522 -0.508 H2 -0.726 -0.703 -0.684 -0.494 -0.485 O9 H1 -0.751 -0.745 -0.719 -0.717 -0.714 H1 -0.743 -0.727 -0.721 -0.706 -0.706 010 V -0.728 -0.726 -0.725 -0.748 -0.768 Vv -0.730 -0.729 -0.731 -0.748 -0.765 Hil TH 0.160 0.161 0.166 0.193 0.190 V 0.160 0.160 0.156 0.166 0.172 H12 V 0.188 0.187 0.185 0.200 0.200 V 0.197 0.196 0.195 0.201 0.202 H13 V 0.191 0.191 0.194 0.206 0.201 V 0.176 0.175 0.173 0.186 0.190 H14 V 0.169 0.164 0.161 0.182 0.205 V 0.180 0.173 0.176 0.183 0.196 H15 V 0.228 0.224 0.234 0.071 0.258 V 0.208 0.206 0.208 0.194 0.239 H16 V 0.194 0.193 0.201 0.188 -0.062 V 0.181 0.168 0.177 0.105 -0.037 H17 V 0.410 0.405 0.373 0.386 0.396 Vv 0.367 0.355 0.345 0.353 0.369 H18 IL 0.398 0.392 0.335 0.238 0.230 LI 0.383 0.366 0.353 0.203 0.202 H19 V 0.415 0.415 0.413 0.407 0.412 V 0.419 0.416 0.414 0.411 0.413 H 20 TH 0.414 0.414 0.426 0.423 0.443 TH 0.417 0.415 0.420 0.435 0.445 *See Table 2 for notation. C-H bonds. They are the C6-H19 and O10-H22 bonds. An increasing flux density generated a considerable negative charge density at the H18 atom. It made the O12- H24 bond relatively slightly polarised, that is, capable of interaction of electrons of that bond with SMF. Effects of the static magnetic field on carbohydrates iy) Z Table 14. Bond lengths [A] in the «- and 8-D-xylopyranose molecules depending on the applied SMF flux density [AFU]*. Bond Flux density [AFU] Tendency 0 0.1 1 10 100 C1-C2 Vv 1.540 1.559 1.553 1.538 1.573 Vv 1.540 1.555 1.535 1.567 1.562 C1-O7 Vv 1.430 1.476 1.603 1.523 1.497 V 1,430 1,433 1.430 1.409 1.416 O7-H17 Vv 0.960 0.965 0.952 0.956 0.953 Vv 0.960 0.971 0.968 0.964 0.951 C1-H11 V 1.090 1.119 1.149 1.097 1.124 V 1.090 1,146 1.160 1.149 1,153 C2-08 V 1.430 1.500 1.516 1.388 1.425 V 1.430 1.504 1.523 1.403 1.431 O8-H18 H3 0.960 1.226 1.565 2.366 3.116 H3 0.960 1,220 1,358 2.532 3.116 C2-H12 V 1.090 1.128 1.159 1.124 1.139 H1 1.090 1,128 1.135 1135 1.136 C2-C3 TH 1.538 1.542 1.580 1.511 1.584 IH 1.537 1.567 1.583 1.602 1.597 C3-O09 Vv 1.430 1.404 1.379 1.407 1.393 Vv 1.430 1.398 1.394 1.397 1.393 O9-H19 Vv 0.960 0.957 0.952 0.953 0.953 Vv 0.960 0.958 0.958 0.958 0.952 C3-H13 V 1.090 1.127 1.152 1.125 1.145 V 1.090 1,132 1.135 1,144 1.140 C3-C4 Vv 1.537 1.609 1.652 1.622 1.630 Vv 1.537 1.614 1.640 1.603 1.624 C4-O10 V 1.430 1.408 1.367 1.412 1.373 Ll 1.430 1.418 1,392 1.380 1.366 O10-H20 H1 0.960 0.973 0.988 0.989 1.002 H1 0.960 0.977 0.978 0.997 1.002 C4-H14 H2 1.090 1.166 1.240 1.270 1.293 H2 1.090 1.169 1.189 1.295 1.309 C4-C5 Vv 1.540 1.553 1.555 1.498 1.519 V 1.540 1.563 1.568 1,492 1.513 C5-H15 H2 1.090 1.184 1.283 1.589 1.878 H2 1.090 1.188 1,221 1.637 1.897 C5-H16 Vv 1.090 1.110 1.108 1.180 1.085 V 1.090 1.118 1.115 1,162 1.104 C5-06 Vv 1.432 1.559 1.482 1.233 1.394 Vv 1.432 1.372 1,446 1.371 1.390 C1-06 Vv 1.432 1.385 1.233 1.439 1.369 Vv 1,432 1,414 1.392 1.419 1.403 *See Table 2 for notation. D-Galactose This aldohexose resides in two anomeric pyranose forms (Fig. 2) interconverting through an open-chain thermodynamically unstable structure. «-D-Galactopyranose (a-D-Galp) can be found in oligo- and polysaccharides, plant mucous and gums and plant glycosides (Maton et al. 1993; Tomasik 1997; Campbell et al. 2006; Tomasik 80 Wojciech Ciesielski et al. / BioRisk 18: 57—91 (2022) f Figure 9. Simplified visualisation of the effect of SMF upon conformation and bond length of «-D- and $-D- xylopyranose anomers (a=c and d-=f respectively) situated in the Cartesian system (see Fig. 2 for notation). Effects of the static magnetic field on carbohydrates 81 Table 15. Charge density [a.u] at particular atoms of the «- and 8-D-glucose molecules depending on SMF flux density [AFU]. Atom Flux density [AFU] Tendency 0 0.1 1.0 10 100 Cl Vv 0.350 0.348 0.353 0.353 0.343 V 0.433 0.431 0.441 0.451 0.451 C2 H1 0.171 0.171 0.180 0.187 0.207 V 0.093 0.092 0.080 0.095 0.068 C3 IL 0.080 0.046 0.029 0.018 0.022 Vv 0.111 0.098 0.073 0.089 0.077 C4 V 0.152 0.178 0.158 0.115 0.029 12 0.123 0.181 0.153 0.097 0.007 C5 H2 -0.018 -0.010 0.084 0.219 0.409 IH -0.044 -0.046 -0.026 0.092 0.342 O6 V -0.622 -0.627 -0.627 -0.618 -0.591 V -0.606 -0.609 -0.615 -0.600 -0.560 O7 H1 -0.680 -0.670 -0.670 -0.669 -0.669 IH -0.675 -0.673 -0.661 -0.647 -0.649 O8 TH -0.694 -0.671 -0.670 -0.665 -0.670 IH -0.705 -0.699 -0.668 -0.687 -0.634 O9 H2 -0.743 -0.721 -0.698 -0.675 -0.568 H2 -0.735 -0.729 -0.709 -0.681 -0.652 O10 H2 -0.742 -0.733 -0.717 -0.695 -0.527 H1 -0.736 -0.735 -0.726 -0.700 -0.661 H11 H2 0.183 0.182 0.184 0.187 0.201 Vv 0.201 0.200 0.195 0.192 0.199 H12 Ll 0.193 0.185 0.176 0.176 0.170 Vv 0.192 0.191 0.172 0.150 0.164 H13 TH 0.199 0.191 0.195 0.205 0.219 V 0.187 0.185 0.184 0.195 0.205 H14 IH 0.193 0.190 0.198 0.205 0.238 V 0.180 0.181 0.178 0.185 0.214 H15 H2 0.177 0.170 0.179 0.190 0.237 V 0.183 0.181 0.176 0.205 0.227 H16 L3 0.172 0.145 0.021 -0.145 -0.506 L3 0.181 0.178 0.140 -0.037 -0.369 H17 Vv 0.399 0.396 0.397 0.398 0.411 Vv 0.387 0.388 0.387 0.376 0.384 H18 Vv 0.397 0.387 0.393 0.391 0.399 Vv 0.398 0.396 0.385 0.398 0.356 H19 L2 0.423 0.427 0.414 0.396 0.291 V 0.418 0.420 0.422 0.399 0.393 H20 H1 0.412 0.415 0.421 0.429 0.456 H1 0.400 0.413 0.419 0.428 0.439 ‘See Table 2 for notation. 2007a; Tomasik 2007b; Heldt and Piechulla 2010; Keung and Mehta 2015; Chu- ruangsuk et al. 2018; Reynolds et al. 2019). Jointly with «-D-glucose, it constitutes lactose, known as milk sugar. In fauna organisms, it is hydrolytically liberated from lactose. In these organisms, it is converted into galactoso-6-phosphate involving ATP a-D-galactose. The latter reacts with galactoso-1-phosphate uridinyltransferase into UDP-galactose which is subsequently transformed with UDP-galactoso-4-epimerase 82 Wojciech Ciesielski et al. / BioRisk 18: 57—91 (2022) Table 16. Bond lengths [A] in the a- and 8-D-xylofuranose molecules depending on the applied SMF flux density [AFU]*. Bond Flux density [AFU] Tendency 0 0.1 1 10 100 C1-C2 H1 1.525 1.555 1.593 1.619 1.666 H1 1.528 1.534 1.562 1.603 1.606 C1-O7 Ll 1.420 1.404 1.398 1.391 1.374 Vv 1.411 1.404 1.395 1.429 1.424 O7-H17 V 0.960 1.037 0.966 1.031 0.972 Vv 0.960 0.954 0.979 1.010 0.975 Cl1-H11 V 1.090 1.143 1.123 1.143 1.178 V 1.091 1.103 1.137 1.106 1.124 C2-C3 Vv 1.528 1.530 1.530 1.536 1.555 Vv 1,532 1.531 1.536 1.548 1.599 C2-08 Ll 1.412 1.382 1.342 1.323 1.292 IL 1.412 1,408 1.369 1.319 1.330 O8-H18 V 0.960 1.101 1.080 1.185 1.187 IH 0.960 0.981 1,142 1.111 1.341 C2-H12 V 1.091 1.110 1.126 1.113 1.179 V 1.091 1,082 1.153 1.166 1,128 C3-C4 Vv 1.540 1.568 1.567 1.569 1.558 H1 1.537 1.542 1.581 1.676 1.659 C3-O9 Vv 1.413 1.372 1.370 1.375 1.391 Vv 1.413 1.405 1.359 1.397 1.307 O9-H19 H2 0.960 1.053 1.171 1.246 1.579 IH 0.960 0.981 1.047 1,321 1.267 C3-H13 V 1.091 1.222 1.225 1.200 1.121 V 1.091 1111 1,231 1,100 1,231 C4-C5 IL 1.533 1.494 1.463 1.448 1.461 IL 1,533 1.523 1,475 1,434 1,449 C5-O10 IL 1.411 1.401 1.401 1.385 1.339 Vv 1.412 1.410 L221 1,336 1.355 O10-H20 Vv 0.960 0.953 0.967 0.957 1.004 V 0.960 0.948 1,189 1.017 0.984 C5-H15 H3 1.090 1.284 1.681 2.068 3.362 H3 1.098 1.418 1.390 1.708 2.636 C5-H16 V 1.091 1.154 1.112 1.123 1.088 V 1.092 PAT 1.151 1,096 1.108 C4-H14 H2 1.091 1.115 1.119 1.123 1.153 V 1.092 1.085 1.142 1.142 1,128 C4-06 H1 1.417 1.438 1.464 1.469 1.472 H1 1,414 1.416 1.454 1,485 1.473 O6-C1 V 1.413 1.418 1.417 1.414 1.421 Vv 1.412 1.412 1.428 1,447 1.417 See Table 2 for notation. into UDP-glucose (Candy 1980). Microbiological oxidation of the CH,OH group of a-D-galactose provides galacturonic acid which essentially inhibits progress of athero- sclerosis (Parikka et al. 2015). Based on computed values of heat of formation, one could note that the «-anomer was more stable than the 8-anomer independently of applied SMF flux density. How- ever, as shown by changes of dipole moment (Table 4), the 8-anomer was more po- Effects of the static magnetic field on carbohydrates 83 f Figure. 10. Simplified visualisation of the effect of SMF upon conformation and bond length of «-D- and 6-D-xylofuranose anomers (a=—c and d-f respectively), situated in the Cartesian system (see Fig. 2 for notation). 84 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) larised with an increase in the flux density. As in anomers of D-glucose, the charge density at particular atoms irregularly varied with increasing flux density. In contrast to anomers of D-glucose, in anomers of D-galactose, the negative charge concentrated at the O7, C5 and C4 atoms and SMF flux density turned it more negative. The nega- tive charge also concentrated at the C2-H14 atom bound to it (Table 5). The positive charge density was noted at the C3 and Cl atoms, as well as the H15 and H13 atoms bound to them, respectively. These effects generated an increase in the corresponding bond lengths (Table 5). Due to an increase in the positive charge at the anomeric C6 atom, one could as- sume a facilitating role of SMF in formation of galactoso-1- phosphate. In addition, the effect of SMF upon the charge density suggested favouring oxidation of D-galac- tose into galacturonic acid. Particular attention should be paid to the C5, C6 and H19 atoms. SMF remark- ably changed their charge distribution. The negative charge shifted to the C5 and H19 atoms, whereas the C6 atom lost this charge to a considerable extent. ‘The strongest in- fluence was evoked by SMF upon the bonds orientated under 45° to the field strength lines, that is, to the x-axis. Extremal elongation was observed for the C6-H19 and O10-H22 bonds (Table 6). Simultaneously, the C6-H18 bond distinctly shortened. It should be underlined that both H18 and H19 were twin atoms bound to the C6 atom. Thus, observed differences could not originate from different intramolecular electronic interactions and completely different situations by those atoms with respect to the SMF line should be responsible for it. Unlike in D-glucose, the positive charge density at the C1 atom decreased with an increase in the flux density. Thus, reactions with any Lewis base would be obstructed. Simultaneously, the flux density up to 0.1 AFU increased the negative charge density at the C6 atom. It would favour phosphorylation at the vicinal hydroxyl group. How- ever, higher flux densities turned the charge density at that atom to positive. Thus, the increase in the charge density with the flux density inhibited that reaction. The susceptibility of D-galactose to the ring opening and to the Maillard reaction depended on its anomer. The C1-O8 bond in the «-anomer varied irregularly with the flux density but, generally, the susceptibility of that anomer to the ring opening was low. That bond in the 8-anomer regularly decreased with an increase in the applied flux density. Simultaneously, the O8-H20 bond was shortened in the «-anomer and elongated in the B-anomer (Table 6). Data shown in Table 6 allowed the visualisation of the effect of SMF upon ano- mers of D-galactose. Structures in Fig. 6 demonstrate a slight effect of SMF upon the conformation of both anomers and significant effect upon the bond lengths of some peripheral C-H bonds. They were the C6-H18 and O10-H22 bonds. An increasing flux density generated a considerable negative charge density at the H22 atom making the C6-H18 bond relatively slightly polarised. Therefore, that bond was capable of interaction with the electrons of that bond with SME In the O10-H22 bond, both its partners carried negative charge. This effect and its origin was the same as that observed in D-glucose anomers. Effects of the static magnetic field on carbohydrates 85 D-Fructose D-Fructose, a ketohexose, is a typical monosaccharide of a floral provenance. In the free form, it resides in fruits, honey and flower nectar. In a bound form, it can be found in several di-, oligo- and polysaccharides, for instance, sucrose, raffinose and inulin, respec- tively. Its presence in the organisms of fauna is a consequence of consumption of plant food. In mammals, free fructose is found in their semen (Maton et al. 1993; Tomasik 1997; Campbell et al. 2006; Tomasik 2007a; Tomasik 2007b; Heldt and Piechulla 2010; Keung and Mehta 2015; Churuangsuk et al. 2018; Reynolds et al. 2019). Humans me- tabolise D-fructose almost entirely in the liver, where it is directed towards replenish- ment of liver glycogen and triglyceride synthesis. In muscles and fat tissues, D-fructose metabolism is initiated by phosphorylation with hexokinase at the O11 atom, turning it into fructose-1-phosphate. The latter enters the glycolysis pathway. In the liver, the metabolism of D-fructose is initiated by fructokinase which forms fructose-1-phosphtate engaging the O10 atoms, respectively (Maton et al. 1993; Tomasik 1997; Hames and Hooper 2004; Campbell et al. 2006; ; Tomasik 2007a; Tomasik 2007b; Heldt and Pie- chulla 2010; Keung and Mehta 2015; Churuangsuk et al. 2018; Reynolds et al. 2019 ). Alcohol fermentation and the Maillard browning reaction are other enzymatic processes common for D-fructose. In the Maillard reaction, the anomeric C1 carbon atom is first engaged (Grandhee and Monnier 1991). D-Fructose resides in four mutually fast interconverting structures, including «-D- fructopyranose («-Frup), 8-D-fructopyranose ($-Frup), «-D-fructofuranose («-Fru/) and 8$- D-fructofuranose (8-D-Fru/) (Fig. 3). Computations of the heat formation (Table 7) pointed to «-D-Frufand «-D-Frup being the most and least stable, respec- tively, amongst the four anomers taken into account (Fig. 3). Applying SMF of 0.1 AFU, the flux density did not change their positions in this group. At 1 AFU, based on that criterion, B-D-Fruf became the most stable, but a further increase in the flux density returned «-D-Fruf to the position of the most stable anomer. «-D-Frup holds the position of the least stable anomer at SMF up to 10 AFU. At 100 AFU, 8-D-Frup became the least stable. The dipole moment of particular anomers also changed with an increase in the applied flux density. However, these changes were in no simple rela- tionship to the stability of particular anomers. It suggested deformation of their initial structure by polarisation of particular bonds. They could also result from departure from their initial situation in the Cartesian system. This was confirmed by comput- ed changes of charge density and bond lengths (Tables 8-11). Inspection of Table 8 showed that, in «- and $-D-fructopyranoses, the negative charge density essential for the phosphorylation reaction at the O12 atom was lower in the «-anomer and it fairly linearly decreased against increasing flux density. Thus, that anomer should be more reactive than the 8-anomer. The Maillard reaction required the positive charge density at the Cl atom. Without SME, the 8-anomer showed a more positive charge at that atom. It decreased against increasing flux density. The «-anomer carried considerably lower positive charge density which additionally decreased against the flux density up to 10 AFU and then increased regularly up to over twice at 100 AFU. 86 Wojciech Ciesielski et al. / BioRisk 18: 57-91 (2022) The strongest changes in the electron density occurred at the Cl, O12«, H13a, H228 and H248 atoms. Thus, both anomers are clearly distinguished from one another. Structural deformations of the «- and 8-D-fructopyranose molecules in SMF (Ta- ble 9 and Fig. 6) resembled those observed for D-glucose and D-galactose anomers. Considerable elongations were observed for the C1-H13, O11-H22 bonds and C6- H19« bonds, whereas the twin C6-H18 bond was only slightly shortened. It was an- other illustration of the importance of the position of the bonds with respect to the SMF field. In the case of D-fructofuranoses, comparison of the negative charge density (Table 10) at the O12 and O11 atoms being potentially the reaction sites for the phospho- rylation suggested that the B-anomer should react more readily than the «-anomer. An increase in the SMF flux density was not beneficial for this reaction as the value of the charge density at these atoms turned less negative. The positive charge density at the C4 and Cl atoms, being the potential reaction site for the Maillard reaction, were higher in the 8-anomer and only slightly decreased with increasing AFU. SMF at 100 AFU generated an essential increase in the positive charge density at the C18, O98, O12« and H21la atoms. At the same time, that charge decreased at the C2, C58, H17a, H24« and particularly at the H208 atom. Anomers of D-fructofuranoses were less susceptible to structural deformations evoked by SMF (Table 11 and Fig. 8). In the «-anomer, the O12-H24, O9-H22 and C5-H17 bonds were longer and that effect was noticeable just at 100 AFU. The 8-anomer was deformed chiefly by elongation of the O9-H22, C1-C2 and O8-H208 bonds. Untypically, the ring was also deformed by the elongation of the C2-C1 bond. D-Xylose D-xylose, aldopentose, is a mono-sugar residing almost exclusively in plants. As a com- ponent of hemicelluloses, it constitutes biomass. In the sphere of fauna, D-xylose was also found in some species of Chrysolinina beetles. It co-constituted cardiac glycosides of their defensive glands (David Morgan 2004). Organisms of fauna receive xylose from their diet. Eukaryotic micro-organisms employ the oxidato-reductase pathway to metabolize D-xylose (Gabaldon et al. 2005). D-xylose is metabolised by humans involving protein xylosyltransferases (XYLT1, XYLT2) which transfer xylose from UDP to a serine in the core protein of proteogly- cans (Stoolmiller et al. 1972; Gotting et al. 2000). Mammals metabolise D-xylose with D-xyloisomerase (Ding et al. 2009; Huntley and Patience 2018). Recently, a highly ef- ficient low-temperature, atmospheric-pressure enzymatic process of the hydrogen pro- duction from D-xylose was presented. It involved thirteen enzymes, including a novel polyphosphate xylulokinase (Del Campo et al. 2013). In another technically important reaction, D-xylose is used for production of furfural, a precursor for synthetic polymers and to tetrahydrofuran (Hoydonck«x et al. 2007). In the initial step, hemicellulose is hydrolysed in an acid-catalysed process (Binder et al. 2010; Millan et al. 2019). That process starts from the protonation of the D-xylopyranose molecule at the O8 atom. Effects of the static magnetic field on carbohydrates 87 It was also found that D-xylose could be useful in therapy of COVID-19 (Cheud- jeu 2020). The latter interacts with D-xylose significantly stimulating the biosynthe- sis of sulphated glycosylamineglycans (GAGs), particularly heparan sulphate (HS). GAGs, especially HS and D-xylose interact with oral non-steroidal anti-inflammatory drugs, active in lung infections. D-Xylose resides in the form of «- and $-xylopyranoses (Xylp) (a and b), as well as a- and B-xylofuranoses (Xyl/) (c and d) (Fig.4). The heat of formation criterion pointed to B-D-xylopyranose as the most stable amongst four anomers of D-xylose (Table 12). It is distinguished from other anomers with a considerably low dipole moment. The increase in the SMF flux density regularly increased the dipole moment of all anomers and, at the same time, destabilised them in terms of their heat of formation values. In both D-xylopyranoses, the metabolic reac- tions should be promoted by the high positive charge density at the O6 atom and low negative charge density at the O8 and O9 atoms. Data in Table 13 showed that the in- fluence of SMF upon the O6, O9 and O8 atoms was negligible, noticeable and strong, respectively. A considerable increase in the positive charge density took place at the Cla, C5 and O8 atoms, whereas its decrease was observed at the C2 and H188 atoms. The SMF flux density promoted reactivity at the C1, especially the Cla atom, slightly promoted reactions at the O9 atom and strongly increased the reactivity of the O8 atom. Taking these arguments under consideration, the «-anomer was more reactive at the C1 atom when residing without SMF and, in SMF, the B-anomer reacted more readily. The reactivity at the O8 atom in the 8-anomer was slightly higher when SMF was applied and the reactivity at the O7 atom in the «-anomer was definitely higher. As shown in Table 14 and Fig. 9, only the O8-H18 bond suffered considerable elongation in SME Less intense elongation was observed at the C4-H14 and C5-H15 bonds in both anomers. ‘That effect was in line with the preference for the elongation of the bonds orientated under approximately 45° with respect to the x-axis. Metabolic processes in D-xylofuranose molecules involved the C1 and O10 atoms. The highly positive and highly negative charge densities, respectively, were beneficial for those reactions. Data in Table 13 showed that, in both anomers, SMF did not influ- ence charge density at the Cl atom. SMF generated a decrease in the negative charge density at the O10 atom. It was particularly noticeable in the «-anomer. It pointed to an inhibition of the reactivity with Lewis acids in these centres. An increase in the posi- tive charge density at the C5a, O9, O10«, H11, H15a and H19 atoms and its decrease at the C48 and H16 atoms confirmed the rule of the importance of 45° orientation of the bonds with respect to the SMF field. Data in Table 16 and Fig. 10 showed that, in both anomers, the C5-H15 bond reacted intensively to an increase in the flux density and the response from the C4-H14 and O9-H19« bonds was weaker. Comparison of the relevant data for D-xylopyranoses and D-xylofuranoses re- vealed that pyranose anomers metabolise more readily. The SMF flux densities ranging from 100 to 10 000 T (0.1 to 100 AFU) employed in performed computations were very high. Experiments performed by Nakamura et al. Takeyama (Nakamura et al. 2018) with SMF of 1200 T (1.2 AFU) resulted in a 88 Wojciech Ciesielski et al. / BioRisk 18: 57—91 (2022) destruction of the generators within few microseconds. The pulse electromagnet con- structed in 2012 at Los Alamos Laboratories remained stable, but producing a field with an intensity of only 100.75 T (approx. 0.1 AFU) (Nguyen et al. 2016). Therefore, only insignificant effects evoked by SMF of flux density of 0.1-100T (0.0001-0.1 AFU) upon carbohydrates could be anticipated in a real life. Conclusions Performed numerical simulations showed the specific influence of static magnetic field (SMF) upon equilibrium constants between particular anomers of the saccharides under study. Their susceptibility to such enzymatic reactions essential for their me- tabolism as phosphorylation with ATP at the CH,OH group, the Entner-Duodoroft metabolic pathway and the Maillard reaction, both also engaging the C1 ring carbon atom in reaction with enzymes and amino acids, is also controlled by SME D-Glucose in SMF takes preferably the «-anomeric form. SMF stimulated its re- activity involving the CH,OH group and the Cl-atom. 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