Research Article |
Corresponding author: Wojciech Ciesielski ( w.ciesielski@interia.pl ) Academic editor: Josef Settele
© 2022 Wojciech Ciesielski, Tomasz Girek, Henryk Kołoczek, Zdzisław Oszczęda, Jacek A. Soroka, Piotr Tomasik.
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.
Citation:
Ciesielski W, Girek T, Kołoczek H, Oszczęda 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
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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 α- and β-D-glucose, α- and β-D-galactose, α- and β-fructopyranoses, α- and β-fructofuranoses and α- and β-D-xylofuranoses and α and β-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 organisms 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.
D-fructose, D-galactose, D-glucose, D-xylose, organisms, static magnetic field
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 polysaccharide, 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 (
In organisms of fauna and their life, the role of carbohydrates is much more complex than in plants. They co-build membranes of body cells and microorganisms colonising 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 (
The effect of increasing environmental pollution with a magnetic field (
This paper presents results of numerical computations applied to selected monosaccharides, that is to α- and β-D-glucose, α- and β-D-galactose, α- and β-fructopyranoses, α- and β-fructofuranoses, α- and β-D-xylopyranoses and α- and β-D-xylofuranoses. They play essential roles in building structure and functioning of organisms of flora and fauna.
Molecular structures were drawn using the Fujitsu SCIGRESS 2.0 software (
In the next step, the tendency of the static magnetic field (SMF) influence, employed as Arbitrary Field Unit (AFU) (1 AFU > 1000 T), upon optimised molecules was computed with Amsterdam Modelling Suite software (
Visualisation of molecules in the coordinate system was performed involving the HyperChem 8.0 software (
Numerical simulations were performed for both anomers of D-glucose (Fig.
Both anomers of D-galactose (Fig.
Both anomers of D-fructopyranoses and both anomers of D-fructofuranoeses (Fig.
Both anomers of D-xylopyranoses and both anomers of D-xylofuranoses (Fig.
Particular structures contain numbering atoms followed in further discussions.
Tables
Results of those computations are visualised in Fig.
Corresponding data computed for anomers of D-galactose are presented in Tables
Tables
Properties computed for anomers of D-fructofuranoses are given in Tables
Corresponding data for D-xylopyranose anomers are provided in Tables
Finally, computations for anomers of D-xylofuranoses are presented in Tables
This study focused on recognising effects of SMF upon metabolism of monosaccharides 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.
SMF could perturb the trajectory of bonds forming electrons involving the Lorentz 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 sp2 to sp3 proportionally to an increase in the flux density. That effect would influence the electrostatic interactions through space within the molecules.
This aldohexose resides chiefly in the cyclic form of α- and β-pyranose (Fig.
Structure of α- and β-D-glucose (a and b respectively) and followed by numbering of atoms.
Both anomers of D-glucose, that is, α- and β-D-glucose are utilied in organisms of flora and fauna as a main source of energy (
One of the important enzymatic reactions of D-glucose, called the Maillard reaction, is known as the enzymatic browning reaction. In the reaction of D-glucose with lysine and arginine, residues of the protein pentosidine are formed (
Performed computations showed that, based on the criterion of heat of formation, the α-D-anomer was slightly more stable than the β-D-anomer (Table
Properties of the α- and β-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] | α | 8.68 | 8.69 | 8.77 | 8.89 | 9.06 |
β | 8.34 | 8.44 | 9.75 | 10.12 | 14.52 | |
Heat of formation [kcal/mole] | α | -1259.6 | -1259.6 | -1248.7 | -1141.5 | -985.8 |
β | -1246.6 | -1245.8 | -1223.5 | -1095.3 | -912.6 |
The charge density at particular atoms of both anomers varied irregularly with an increase in the flux density (Table
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on SMF flux density [AFU].
Atom | Fluxdensity[AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
C1 | H1 | 0.421 | 0.428 | 0.430 | 0.435 | 0.434 |
L2 | 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 |
L1 | 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 | IH | -0.639 | -0.636 | -0.632 | -0.620 | -0.628 |
H2 | -0.631 | -0.620 | -0.610 | -0.598 | -0.017 | |
O8 | L2 | -0.697 | -0.706 | -0.715 | -0.734 | -0.736 |
H2 | -0.727 | -0.708 | -0.702 | -0.696 | -0.688 | |
O9 | IH | -0.706 | -0.708 | -0.708 | -0.689 | -0.683 |
H | -0.752 | -0.750 | -0.740 | -0.716 | -0.696 | |
O10 | IH | -0.752 | -0.745 | -0.721 | -0.475 | -0.551 |
H2 | -0.745 | -0.712 | -0.580 | -0.489 | -0.634 | |
O11 | V | -0.744 | -0.741 | -0.738 | -0.724 | -0.740 |
V | -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 | IH | 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 | V | 0.395 | 0.396 | 0.393 | 0.393 | 0.396 |
L1 | 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 |
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 computation for the twin hydrogen H18 and H19 atoms. Due to accepted computation methodology, 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
Generally, atoms of the pyranose skeleton were moderately sensitive to SMF, although increasing SMF flux density considerably decreased basicity of the ring O5 atom in the β-anomer. The O and H atoms were the most and least sensitive, respectively, to the effect of SMF. 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 appeared 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
An insight into the effect of SMF upon the length of bonds in the molecules of both anomers (Table
Bond lengths [Ǻ] in the α- and β-D-glucose molecules depending on the applied SMF flux density [AFU]a.
Bond | Flux density [AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1 | 10 | 100 | |
C1-C2 | H1 | 1.530 | 1.536 | 1.554 | 1.579 | 1.587 |
H1 | 1.528 | 1.533 | 1.534 | 1.539 | 1.552 | |
C1-O8 | L1 | 1.413 | 1.413 | 1.408 | 1.389 | 1.394 |
L1 | 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-O9 | 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 | V | 1.527 | 1.518 | 1.514 | 1.525 | 1.523 |
V | 1.527 | 1.514 | 1.517 | 1.530 | 1.534 | |
C3-O10 | V | 1.412 | 1.416 | 1.423 | 1.381 | 1.397 |
V | 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 | V | 1.533 | 1.529 | 1.531 | 1.529 | 1.525 |
V | 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 |
V | 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 | 1.375 | 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 | 1.175 | 1.189 | |
C6-H19 | H3 | 1.099 | 1.262 | 1.444 | 2.675 | 3.259 |
H3 | 1.099 | 1.410 | 1.771 | 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-C1 | L1 | 1.433 | 1.414 | 1.392 | 1.387 | 1.375 |
V | 1.432 | 1.402 | 1.3942 | 1.400 | 1.403 |
Visualisation of the data from Table
This aldohexose resides in two anomeric pyranose forms (Fig.
Structure of α- and β-D-galactose (a and b respectively) and followed by numbering of atoms.
Based on computed values of heat of formation, one could note that the α-anomer was more stable than the β-anomer independently of applied SMF flux density. However, as shown by changes of dipole moment (Table
Properties of the α- and β-D-galactose 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] | α | 8.63 | 8.72 | 8.83 | 8.93 | 9.18 |
β | 8.66 | 8.72 | 8.88 | 8.98 | 9.32 | |
Heat of formation [kcal/mole] | α | -1286.3 | -1285.2 | -1267.4 | -1206.5 | -1128.4 |
β | -1252.3 | -1251.2 | -1247.4 | -1198.7 | -1111.3 |
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on SMF flux density [AFU].
Atom | Flux density [AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
C1 | 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 |
IH | 0.191 | 0.197 | 0.200 | 0.185 | 0.210 | |
C3 | IL | 0.102 | 0.131 | 0.086 | 0.040 | 0.099 |
L1 | 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 | V | -0.747 | -0.746 | -0.745 | -0.742 | -0.772 |
V | -0.728 | -0.721 | -0.713 | -0.700 | -0.733 | |
O10 | V | -0.747 | -0.758 | -0.607 | -0.502 | -0.712 |
V | -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 |
V | 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 | IH | 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 |
IH | 0.182 | 0.166 | 0.169 | 0.214 | 0.283 | |
H19 | L2 | 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 | L1 | 0.461 | 0.446 | 0.414 | 0.384 | 0.325 |
L1 | 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 |
Due to an increase in the positive charge at the anomeric C6 atom, one could assume 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-galactose into galacturonic acid.
Particular attention should be paid to the C5, C6 and H19 atoms. SMF remarkably 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 influence 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
Bond lengths [Ǻ] in the α- and β-D-galactose molecules depending on the applied SMF flux density [AFU]a.
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 | V | 1.515 | 1.497 | 1.504 | 1.576 | 1.536 |
V | 1.537 | 1.520 | 1.505 | 1.510 | 1.543 | |
C2-O9 | V | 1.408 | 1.390 | 1.386 | 1.390 | 1.410 |
IL | 1.430 | 1.416 | 1.394 | 1.386 | 1.424 | |
O9-H21 | V | 0.979 | 1.003 | 0.962 | 0.991 | 0.955 |
V | 0.960 | 1.013 | 1.014 | 0.998 | 0.972 | |
C2-H14 | V | 1.100 | 1.189 | 1.171 | 1.212 | 1.166 |
IH | 1.090 | 1.137 | 1.171 | 1.180 | 1.159 | |
C3-C4 | V | 1.512 | 1.509 | 1.515 | 1.519 | 1.513 |
V | 1.537 | 1.532 | 1.522 | 1.532 | 1.528 | |
C3-O10 | V | 1.407 | 1.490 | 1.380 | 1.364 | 1.381 |
L1 | 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 |
IH | 1.090 | 1.117 | 1.139 | 1.121 | 1.144 | |
C4-C5 | L1 | 1.539 | 1.525 | 1.521 | 1.512 | 1.509 |
IL | 1.540 | 1.535 | 1.534 | 1.532 | 1.533 | |
C4-O11 | V | 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 |
IH | 1.090 | 1.111 | 1.130 | 1.117 | 1.138 | |
C5-C6 | IL | 1.534 | 1.489 | 1.448 | 1.437 | 1.479 |
V | 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 | 1.127 | 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 |
L2 | 1.430 | 1.417 | 1.374 | 1.314 | 1.274 | |
C6-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 |
V | 1.090 | 1.158 | 1.177 | 1.434 | 1.152 | |
C5-O7 | V | 1.432 | 1.437 | 1.440 | 1.439 | 1.432 |
V | 1.433 | 1.434 | 1.437 | 1.434 | 1.429 | |
O7-C1 | V | 1.431 | 1.420 | 1.419 | 1.428 | 1.430 |
V | 1.433 | 1.430 | 1.427 | 1.442 | 1.456 |
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. However, 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 α-anomer varied irregularly with the flux density but, generally, the susceptibility of that anomer to the ring opening was low. That bond in the β-anomer regularly decreased with an increase in the applied flux density. Simultaneously, the O8-H20 bond was shortened in the α-anomer and elongated in the β-anomer (Table
Data shown in Table
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, respectively. Its presence in the organisms of fauna is a consequence of consumption of plant food. In mammals, free fructose is found in their semen (
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 (
D-Fructose resides in four mutually fast interconverting structures, including α-D-fructopyranose (α-Frup), β-D-fructopyranose (β-Frup), α-D-fructofuranose (α-Fruf) and β- D-fructofuranose (β-D-Fruf) (Fig.
Properties of the α- and β-D-fructopyranose and corresponding α- and β-D-fructofuranose molecules situated along the x-axis of the Cartesian system in SMF of the flux density of 0 to 100 AFUa.
Property | Anomer | Flux density [AFU] | ||||
---|---|---|---|---|---|---|
0 | 0.1 | 1 | 10 | 100 | ||
Dipole moment [D] | α-D-Frup | 3.63 | 3.67 | 3.76 | 3.93 | 4.24 |
β-D-Frup | 3.60 | 3.61 | 3.69 | 3.86 | 4.16 | |
α-D-Fruf | 3.68 | 3.69 | 3.87 | 3.92 | 4.16 | |
β-D-Fruf | 3.66 | 3.71 | 3.85 | 3.90 | 4.09 | |
Heat of formation [kcal/mole] | α-D-Frup | -1193.2 | -1190.4 | -1153.8 | -1140.6 | -1096.5 |
β-D-Frup | -1205.5 | -1203.2 | -1199.9 | -1156.7 | -1026.5 | |
α-D-Fruf | -1255.6 | -1253.5 | -1231.5 | -1231.5 | -1201.8 | |
β-D-Fruf | -1245.6 | -1243.5 | -1238.6 | -1221.4 | -1198.5 |
Charge density [a.u] at particular atoms of the α- and β-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 | V | 0.541 | 0.576 | 0.552 | 0.552 | 0.487 |
V | 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 | V | -0.578 | -0.578 | -0.570 | -0.561 | -0.540 |
V | -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 | |
O10 | V | -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 |
V | -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 | L1 | 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 |
IH | 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 |
IH | 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 | V | 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 |
Structure of α- and β-D-fructopyranoses (a and b respectively) and α- and β-D-fructofuranoses (c and d respectively) and followed by numbering of atoms.
The strongest changes in the electron density occurred at the C1, O12α, H13α, H22β and H24β atoms. Thus, both anomers are clearly distinguished from one another.
Structural deformations of the α- and β-D-fructopyranose molecules in SMF (Table
Bond lengths [Ǻ] in the α- and β-D-fructopyranose molecules depending on the applied SMF flux density [AFU]a.
Bond | Flux density [AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1 | 10 | 100 | |
C1-C2 | V | 1.540 | 1.575 | 1.561 | 1.563 | 1.571 |
V | 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 | V | 1.537 | 1.559 | 1.544 | 1.568 | 1.519 |
V | 1.537 | 1.531 | 1.546 | 1.544 | 1.541 | |
C2-O8 | 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 | V | 1.537 | 1.562 | 1.570 | 1.568 | 1.566 |
IH | 1.537 | 1.546 | 1.564 | 1.571 | 1.524 | |
C3-O10 | V | 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 |
H1 | 1.540 | 1.547 | 1.560 | 1.575 | 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 | 4.491 | |
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 |
IH | 1.540 | 1.516 | 1.560 | 1.567 | 1.570 | |
C5-O9 | 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 | 1.375 | |
O12-H24 | V | 0.960 | 0.963 | 0.932 | 0.974 | 0.928 |
V | 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 | |
C6-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 | V | 1.433 | 1.387 | 1.397 | 1.393 | 1.416 |
V | 1.432 | 1.417 | 1.392 | 1.402 | 1.400 | |
O7-C1 | IH | 1.433 | 1.467 | 1.477 | 1.485 | 1.462 |
V | 1.433 | 1.454 | 1.481 | 1.470 | 1.470 |
In the case of D-fructofuranoses, comparison of the negative charge density (Table
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on SMF flux density [AFU].
Atom | Flux density [AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
C1 | 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 |
L1 | 0.092 | 0.080 | 0.079 | 0.071 | 0.032 | |
C5 | IH | 0.097 | 0.086 | 0.109 | 0.206 | 0.405 |
L2 | 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 | V | -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 |
IH | -0.734 | -0.712 | -0.714 | -0.699 | -0.667 | |
O11 | 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 |
IH | 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 |
V | 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 | V | 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 |
V | 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 |
Anomers of D-fructofuranoses were less susceptible to structural deformations evoked by SMF (Table
Bond lengths [Ǻ] in the α- and β-D-fructofuranose molecules depending on the applied SMF flux density [AFU]a.
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 | H1 | 0.960 | 0.955 | 0.970 | 0.978 | 0.985 |
H3 | 0.960 | 0.994 | 1.155 | 1.183 | 1.783 | |
C1-C5 | L1 | 1.535 | 1.521 | 1.511 | 1.502 | 1.495 |
IL | 1.540 | 1.527 | 1.509 | 1.473 | 1.485 | |
C5-O11 | IH | 1.412 | 1.389 | 1.586 | 1.376 | 1.848 |
V | 1.430 | 1.439 | 1.442 | 1.421 | 1.370 | |
O11-H21 | V | 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 | V | 1.523 | 1.514 | 1.513 | 1.519 | 1.541 |
IL | 1.539 | 1.536 | 1.497 | 1.477 | 1.522 | |
C2-O9 | V | 1.412 | 1.422 | 1.427 | 1.426 | 1.395 |
V | 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-O10 | 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 |
V | 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 |
V | 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 | |
C6-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 |
V | 0.960 | 0.990 | 0.961 | 0.927 | 0.958 | |
C6-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 | 1.257 | 1.290 |
IH | 1.090 | 1.139 | 1.147 | 1.139 | 1.155 | |
O7-C1 | L1 | 1.421 | 1.420 | 1.420 | 1.417 | 1.409 |
V1 | 1.431 | 1.457 | 1.437 | 1.402 | 1.412 |
D-xylose, aldopentose, is a mono-sugar residing almost exclusively in plants. As a component 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 (
Organisms of fauna receive xylose from their diet. Eukaryotic micro-organisms employ the oxidato-reductase pathway to metabolize D-xylose (
It was also found that D-xylose could be useful in therapy of COVID-19 (
D-Xylose resides in the form of α- and β-xylopyranoses (Xylp) (a and b), as well as α- and β-xylofuranoses (Xylf) (c and d) (Fig.
Structure of α- and β-D-xylopyranoses (a and b respectively) and α- and β-D-xylofuranoses (c and d respectively) and followed by numbering of atoms.
The heat of formation criterion pointed to β-D-xylopyranose as the most stable amongst four anomers of D-xylose (Table
Properties of the α- and β-D-xylose molecules situated along the x-axis of the Cartesian system in SMF of the flux density of 0 to 100 AFUa.
Property | Anomer | Flux density [AFU] | ||||
---|---|---|---|---|---|---|
0 | 0.1 | 1 | 10 | 100 | ||
Dipole moment [D] | α-D-Xylp | 4.22 | 4.24 | 4.31 | 4.67 | 4.73 |
β-D-Xylp | 1.22 | 1.23 | 1.29 | 1.37 | 1.47 | |
α-D-Xylf | 4.85 | 4.89 | 4.94. | 5.15 | 5.69 | |
β-D-Xylf | 4.87 | 4.89 | 4.95 | 5.01 | 5.19 | |
Heat of formation [kcal/mole] | α-D-Xylp | -1143.2 | -1127.4 | -1089.6 | -1061.2 | -1005.4 |
β-D-Xylp | -1154.2 | 1147.3 | -1110.3 | -1089.5 | -1021.8 | |
α-D-Xylf | -1076.2 | —1075.4 | -1069.4 | -1041.3 | -995.6 | |
β-D-Xylf | -1051.2 | -1049.5 | -1036.4 | -1004.4 | -952.3 |
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on SMF flux density [AFU].
Atom | Flux density [AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
C1 | H2 | 0.388 | 0.400 | 0.424 | 0.450 | 0.460 |
V | 0.474 | 0.476 | 0.460 | 0.478 | 0.492 | |
C2 | L2 | 0.093 | 0.085 | 0.035 | -0.039 | -0.059 |
L2 | 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 | IH | 0.142 | 0.145 | 0.161 | 0.172 | 0.167 |
IH | 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 |
V | -0.590 | -0.590 | -0.585 | -0.569 | -0.577 | |
O7 | V | -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 | |
O10 | V | -0.728 | -0.726 | -0.725 | -0.748 | -0.768 |
V | -0.730 | -0.729 | -0.731 | -0.748 | -0.765 | |
H11 | IH | 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 |
V | 0.367 | 0.355 | 0.345 | 0.353 | 0.369 | |
H18 | IL | 0.398 | 0.392 | 0.335 | 0.238 | 0.230 |
L1 | 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 | IH | 0.414 | 0.414 | 0.426 | 0.423 | 0.443 |
IH | 0.417 | 0.415 | 0.420 | 0.435 | 0.445 |
Simplified visualisation of the effect of SMF upon conformation and bond length of α-D- and β-D-glucose anomers (a–c and d–f respectively), situated in the Cartesian system.
Simplified visualisation of the effect of SMF upon conformation and bond length of α-D- and β-D-galactose anomers (a–c and d–f respectively), situated in the Cartesian system. (see Fig.
Simplified visualisation of the effect of SMF upon conformation and bond length of α-D- and β-D-fructopyranose anomers (a–c and d–f respectively), situated in the Cartesian system (see Fig.
Simplified visualisation of the effect of SMF upon conformation and bond length of α-D- and β-D-fructofuranose anomers (a–c and d–f respectively), situated in the Cartesian system (see Fig.
As shown in Table
Bond lengths [Ǻ] in the α- and β-D-xylopyranose molecules depending on the applied SMF flux density [AFU]a.
Bond | Flux density [AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1 | 10 | 100 | |
C1-C2 | V | 1.540 | 1.559 | 1.553 | 1.538 | 1.573 |
V | 1.540 | 1.555 | 1.535 | 1.567 | 1.562 | |
C1-O7 | V | 1.430 | 1.476 | 1.603 | 1.523 | 1.497 |
V | 1.430 | 1.433 | 1.430 | 1.409 | 1.416 | |
O7-H17 | V | 0.960 | 0.965 | 0.952 | 0.956 | 0.953 |
V | 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-O8 | 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 | 1.135 | 1.136 | |
C2-C3 | IH | 1.538 | 1.542 | 1.580 | 1.511 | 1.584 |
IH | 1.537 | 1.567 | 1.583 | 1.602 | 1.597 | |
C3-O9 | V | 1.430 | 1.404 | 1.379 | 1.407 | 1.393 |
V | 1.430 | 1.398 | 1.394 | 1.397 | 1.393 | |
O9-H19 | V | 0.960 | 0.957 | 0.952 | 0.953 | 0.953 |
V | 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 | V | 1.537 | 1.609 | 1.652 | 1.622 | 1.630 |
V | 1.537 | 1.614 | 1.640 | 1.603 | 1.624 | |
C4-O10 | V | 1.430 | 1.408 | 1.367 | 1.412 | 1.373 |
L1 | 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 | V | 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 | V | 1.090 | 1.110 | 1.108 | 1.180 | 1.085 |
V | 1.090 | 1.118 | 1.115 | 1.162 | 1.104 | |
C5-O6 | V | 1.432 | 1.559 | 1.482 | 1.233 | 1.394 |
V | 1.432 | 1.372 | 1.446 | 1.371 | 1.390 | |
C1-O6 | V | 1.432 | 1.385 | 1.233 | 1.439 | 1.369 |
V | 1.432 | 1.414 | 1.392 | 1.419 | 1.403 |
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on SMF flux density [AFU].
Atom | Flux density [AFU] | |||||
---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
C1 | V | 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 |
V | 0.111 | 0.098 | 0.073 | 0.089 | 0.077 | |
C4 | V | 0.152 | 0.178 | 0.158 | 0.115 | 0.029 |
L2 | 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 | IH | -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 |
V | 0.201 | 0.200 | 0.195 | 0.192 | 0.199 | |
H12 | L1 | 0.193 | 0.185 | 0.176 | 0.176 | 0.170 |
V | 0.192 | 0.191 | 0.172 | 0.150 | 0.164 | |
H13 | IH | 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 | V | 0.399 | 0.396 | 0.397 | 0.398 | 0.411 |
V | 0.387 | 0.388 | 0.387 | 0.376 | 0.384 | |
H18 | V | 0.397 | 0.387 | 0.393 | 0.391 | 0.399 |
V | 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 |
Simplified visualisation of the effect of SMF upon conformation and bond length of α-D- and β-D-xylopyranose anomers (a–c and d–f respectively) situated in the Cartesian system (see Fig.
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
Bond lengths [Ǻ] in the α- and β-D-xylofuranose molecules depending on the applied SMF flux density [AFU]a.
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 | L1 | 1.420 | 1.404 | 1.398 | 1.391 | 1.374 |
V | 1.411 | 1.404 | 1.395 | 1.429 | 1.424 | |
O7-H17 | V | 0.960 | 1.037 | 0.966 | 1.031 | 0.972 |
V | 0.960 | 0.954 | 0.979 | 1.010 | 0.975 | |
C1-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 | V | 1.528 | 1.530 | 1.530 | 1.536 | 1.555 |
V | 1.532 | 1.531 | 1.536 | 1.548 | 1.599 | |
C2-O8 | L1 | 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 | V | 1.540 | 1.568 | 1.567 | 1.569 | 1.558 |
H1 | 1.537 | 1.542 | 1.581 | 1.676 | 1.659 | |
C3-O9 | V | 1.413 | 1.372 | 1.370 | 1.375 | 1.391 |
V | 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 | 1.111 | 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 |
V | 1.412 | 1.410 | 1.221 | 1.336 | 1.355 | |
O10-H20 | V | 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 | 1.121 | 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-O6 | 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 |
V | 1.412 | 1.412 | 1.428 | 1.447 | 1.417 |
Simplified visualisation of the effect of SMF upon conformation and bond length of α-D- and β-D-xylofuranose anomers (a–c and d–f respectively), situated in the Cartesian system (see Fig.
Comparison of the relevant data for D-xylopyranoses and D-xylofuranoses revealed 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 (
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 metabolism as phosphorylation with ATP at the CH2OH group, the Entner-Duodoroff 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 SMF.
D-Glucose in SMF takes preferably the α-anomeric form. SMF stimulated its reactivity involving the CH2OH group and the C1-atom.
D-Galactose in SMF takes preferably the α-anomeric form. The reactivity at the CH2OH group and C1 atom vary irregularly with an increase of the applied flux density.
D-Fructose in SMF takes preferably the α-D-Fruf form and D-xylose under such conditions takes preferably the β-D-Xylp form. Their susceptibility to the reactions important for their metabolism irregularly vary with the applied flux density.
Only insignificant effects evoked by SMF of flux density of 0.1–100T upon carbohydrates could be anticipated in a real life.