Corresponding author: Wojciech Ciesielski (
Academic editor: Josef Settele
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
Ciesielski W, Girek T, Kołoczek 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.
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
Molecular structures were drawn using the Fujitsu SCIGRESS 2.0 software (
In the next step, the tendency of the static magnetic field (
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
This aldohexose resides chiefly in the cyclic form of α- and β-pyranose (Fig.
Structure of α- and β-D-glucose (
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
Property | Anomer | Flux density [ |
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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
Atom | Fluxdensity[ |
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Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
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O12 | V | -0.711 | -0.715 | -0.716 | -0.669 | -0.651 |
H1 | - |
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H17 | IH | 0.186 | 0.185 | 0.186 | 0.228 | 0.230 |
H1 |
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H18 | L3 | 0.155 | 0.130 | 0.075 | -0.479 | -0.493 |
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H19 | IH | 0.186 | 0.183 | 0.185 | 0.256 | 0.278 |
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H20 | H1 | 0.406 | 0.409 | 0.412 | 0.438 | 0.439 |
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H21 | V | 0.395 | 0.396 | 0.393 | 0.393 | 0.396 |
L1 |
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H22 | L3 | 0.405 | 0.396 | 0.370 | 0.120 | 0.087 |
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H23 | V | 0.417 | 0.417 | 0.416 | 0.422 | 0.433 |
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H24 | H2 | 0.395 | 0.407 | 0.421 | 0.502 | 0.523 |
H2 |
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aData in normal font and in italics are for α- and β-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.
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
Review of Table
An insight into the effect of
Bond lengths [Ǻ] in the α- and β-D-glucose molecules depending on the applied
Bond | Flux density [ |
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Tendency | 0 | 0.1 | 1 | 10 | 100 | |
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O8-H20 | H1 | 0.972 | 1.011 | 1.048 | 1.041 | 1.045 |
V |
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O9-H21 | V | 0.972 | 1.007 | 1.004 | 1.004 | 0.993 |
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O10-H22 | H3 | 0.972 | 1.198 | 1.389 | 3.084 | 3.685 |
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O11-H23 | V | 0.972 | 0.968 | 0.972 | 0.964 | 0.964 |
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C5-C6 | H1 | 1.528 | 1.531 | 1.540 | 1.556 | 1.570 |
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C6-O12 | IL | 1.412 | 1.392 | 1.368 | 1.292 | 1.298 |
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O12-H24 | H | 0.972 | 0.995 | 1.011 | 1.050 | 1.058 |
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C6-H18 | H2 | 1.099 | 1.148 | 1.150 | 1.168 | 1.169 |
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C6-H19 | H3 | 1.099 | 1.262 | 1.444 | 2.675 | 3.259 |
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aSee Table
Visualisation of the data from Table
This aldohexose resides in two anomeric pyranose forms (Fig.
Structure of α- and β-D-galactose (
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
Properties of the α- and β-D-galactose molecules situated along the x-axis of the Cartesian system in
Property | Anomer | Flux density [ |
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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
Atom | Flux density [ |
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Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
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O12 | H | -0.758 | -0.727 | -0.677 | -0.619 | -0.534 |
H | - |
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H18 | H1 | 0.205 | 0.204 | 0.239 | 0.283 | 0.301 |
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H19 | L2 | 0.181 | 0.093 | -0.277 | -0.496 | -0.315 |
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H20 | H1 | 0.431 | 0.436 | 0.443 | 0.451 | 0.457 |
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H21 | V | 0.435 | 0.433 | 0.422 | 0.423 | 0.434 |
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H22 | IL | 0.445 | 0.449 | 0.443 | 0.209 | 0.078 |
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H23 | L1 | 0.461 | 0.446 | 0.414 | 0.384 | 0.325 |
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H24 | H1 | 0.425 | 0.438 | 0.455 | 0.480 | 0.487 |
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aSee Table
Due to an increase in the positive charge at the anomeric C6 atom, one could assume a facilitating role of
Particular attention should be paid to the C5, C6 and H19 atoms.
Bond lengths [Ǻ] in the α- and β-D-galactose molecules depending on the applied
Bond | Tendency | Flux density [ |
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0 | 0.1 | 1 | 10 | 100 | ||
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O8-H20 | V | 0.978 | 0.974 | 0.962 | 0.974 | 0.966 |
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O9-H21 | V | 0.979 | 1.003 | 0.962 | 0.991 | 0.955 |
V |
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O10-H22 | H3 | 0.922 | 1.345 | 2.062 | 2.947 | 4.432 |
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O11-H23 | V | 0.982 | 0.932 | 1.005 | 0.932 | 0.972 |
V |
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C6-O12 | V | 1.100 | 1.543 | 1.099 | 1.210 | 1.123 |
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O12-H24 | V | 0.975 | 1.013 | 0.988 | 1.033 | 1.000 |
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C6-H18 | L2 | 1.418 | 1.404 | 1.380 | 1.346 | 1.339 |
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C6-H19 | H3 | 1.100 | 1.108 | 2.360 | 3.401 | 5.114 |
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aSee Table
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
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-Fru
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
Property | Anomer | Flux density [ |
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0 | 0.1 | 1 | 10 | 100 | ||
Dipole moment [D] | α-D-Fru |
3.63 | 3.67 | 3.76 | 3.93 | 4.24 |
β-D-Fru |
3.60 | 3.61 | 3.69 | 3.86 | 4.16 | |
α-D-Fru |
3.68 | 3.69 | 3.87 | 3.92 | 4.16 | |
β-D-Fru |
3.66 | 3.71 | 3.85 | 3.90 | 4.09 | |
Heat of formation [kcal/mole] | α-D-Fru |
-1193.2 | -1190.4 | -1153.8 | -1140.6 | -1096.5 |
β-D-Fru |
-1205.5 | -1203.2 | -1199.9 | -1156.7 | -1026.5 | |
α-D-Fru |
-1255.6 | -1253.5 | -1231.5 | -1231.5 | -1201.8 | |
β-D-Fru |
-1245.6 | -1243.5 | -1238.6 | -1221.4 | -1198.5 |
aUpper and lower values (in italics) are for α- and β-isomers, respectively.
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on
Atom | Flux density [ |
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Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
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O12 | H2 | -0.691 | -0.660 | -0.662 | -0.657 | -0.540 |
IL | - |
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H18 | V | 0.165 | 0.157 | 0.149 | 0.146 | 0.179 |
V |
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H19 | V | 0.159 | 0.200 | 0.202 | 0.212 | 0.142 |
V |
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H20 | H2 | 0.360 | 0.422 | 0.434 | 0.446 | 0.467 |
V |
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H21 | V | 0.386 | 0.413 | 0.411 | 0.423 | 0.420 |
V |
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H22 | V | 0.418 | 0.116 | 0.099 | 0.110 | 0.130 |
L2 |
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H23 | V | 0.416 | 0.316 | 0.358 | 0.372 | 0.387 |
V |
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H24 | V | 0.390 | 0.363 | 0.372 | 0.372 | 0.375 |
H2 |
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aSee Table
Structure of α- and β-D-fructopyranoses (
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
Bond lengths [Ǻ] in the α- and β-D-fructopyranose molecules depending on the applied
Bond | Flux density [ |
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Tendency | 0 | 0.1 | 1 | 10 | 100 | |
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O8-H20 | V | 0.960 | 1.026 | 0.968 | 1.026 | 1.017 |
V |
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O10-H21 | V | 0.960 | 0.986 | 0.916 | 1.017 | 0.907 |
V |
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O11-H22 | H3 | 0.960 | 2.268 | 2.928 | 3.341 | 3.781 |
H3 |
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O9-H23 | V | 0.960 | 1.035 | 0.910 | 1.016 | 0.897 |
V |
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C6-O12 | V | 1.430 | 1.556 | 1.471 | 1.435 | 1.423 |
IL |
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O12-H24 | V | 0.960 | 0.963 | 0.932 | 0.974 | 0.928 |
V |
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C6-H18 | V | 0.960 | 1.101 | 1.119 | 1.080 | 1.111 |
IL |
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C6-H19 | H2 | 1.090 | 1.128 | 1.154 | 1.157 | 1.569 |
V |
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aSee Table
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
Atom | Flux density [ |
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---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
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O11 | H1 | -0.674 | -0.641 | -0.620 | -0.605 | -0.580 |
H1 | - |
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O12 | H2 | -0.696 | -0.682 | -0.644 | -0.500 | -0.359 |
IH | - |
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H16 | H1 | 0.167 | 0.170 | 0.178 | 0.196 | 0.244 |
V |
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H17 | L2 | 0.104 | 0.064 | -0.004 | -0.148 | -0.470 |
H1 |
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H18 | VI | 0.169 | 0.161 | 0.159 | 0.175 | 0.248 |
H |
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H19 | V | 0.148 | 0.142 | 0.143 | 0.154 | 0.171 |
V |
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H20 | V | 0.365 | 0.364 | 0.366 | 0.374 | 0.388 |
V |
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H21 | H2 | 0.389 | 0.395 | 0.402 | 0.419 | 0.454 |
V |
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H22 | L2 | 0.387 | 0.373 | 0.355 | 0.341 | 0.295 |
L2 |
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H23 | V | 0.403 | 0.400 | 0.397 | 0.398 | 0.407 |
V |
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H24 | L3 | 0.388 | 0.373 | 0.335 | 0.198 | 0.005 |
V |
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aSee Table
Anomers of D-fructofuranoses were less susceptible to structural deformations evoked by
Bond lengths [Ǻ] in the α- and β-D-fructofuranose molecules depending on the applied
Bond | Flux density [ |
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---|---|---|---|---|---|---|
tendency | 0 | 0.1 | 1 | 10 | 100 | |
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O8-H20 | H1 | 0.960 | 0.955 | 0.970 | 0.978 | 0.985 |
H3 |
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C5-O11 | IH | 1.412 | 1.389 | 1.586 | 1.376 | 1.848 |
V |
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O11-H21 | V | 0.960 | 0.960 | 0.970 | 0.978 | 0.995 |
V |
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C5-H16 | V | 1.091 | 1.151 | 1.150 | 1.121 | 1.112 |
V |
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C5-H17 | H3 | 1.091 | 1.365 | 1.586 | 1.936 | 2.922 |
V |
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O9-H22 | H3 | 0.959 | 1.173 | 1.322 | 1.487 | 2.036 |
H3 |
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C2-H13 | H1 | 1.092 | 1.109 | 1.120 | 1.124 | 1.153 |
V |
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O10-H23 | V | 0.960 | 1.000 | 1.000 | 0.983 | 0.946 |
V |
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C6-O12 | IL | 1.411 | 1.417 | 1.410 | 1.391 | 1.360 |
V |
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O12-H24 | H3 | 0.960 | 1.166 | 1.378 | 1.902 | 3.080 |
V |
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C6-H18 | V | 1.090 | 1.134 | 1.132 | 1.122 | 1.122 |
V |
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C6-H19 | H2 | 1.098 | 1.190 | 1.246 | 1.257 | 1.290 |
IH |
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aSee Table
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
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 (Xyl
Structure of α- and β-D-xylopyranoses (
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
Property | Anomer | Flux density [ |
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---|---|---|---|---|---|---|
0 | 0.1 | 1 | 10 | 100 | ||
Dipole moment [D] | α-D-Xyl |
4.22 | 4.24 | 4.31 | 4.67 | 4.73 |
β-D-Xyl |
1.22 | 1.23 | 1.29 | 1.37 | 1.47 | |
α-D-Xyl |
4.85 | 4.89 | 4.94. | 5.15 | 5.69 | |
β-D-Xyl |
4.87 | 4.89 | 4.95 | 5.01 | 5.19 | |
Heat of formation [kcal/mole] | α-D-Xyl |
-1143.2 | -1127.4 | -1089.6 | -1061.2 | -1005.4 |
β-D-Xyl |
-1154.2 | 1147.3 | -1110.3 | -1089.5 | -1021.8 | |
α-D-Xyl |
-1076.2 | —1075.4 | -1069.4 | -1041.3 | -995.6 | |
β-D-Xyl |
-1051.2 | -1049.5 | -1036.4 | -1004.4 | -952.3 |
aUpper and lower values (in italics) are for α- and β-isomers, respectively.
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on
Atom | Flux density [ |
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Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
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H17 | V | 0.410 | 0.405 | 0.373 | 0.386 | 0.396 |
V |
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H18 | IL | 0.398 | 0.392 | 0.335 | 0.238 | 0.230 |
L1 |
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H19 | V | 0.415 | 0.415 | 0.413 | 0.407 | 0.412 |
V |
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H 20 | IH | 0.414 | 0.414 | 0.426 | 0.423 | 0.443 |
IH |
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aSee Table
Simplified visualisation of the effect of
Simplified visualisation of the effect of
Simplified visualisation of the effect of
Simplified visualisation of the effect of
As shown in Table
Bond lengths [Ǻ] in the α- and β-D-xylopyranose molecules depending on the applied
Bond | Flux density [ |
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---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1 | 10 | 100 | |
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O7-H17 | V | 0.960 | 0.965 | 0.952 | 0.956 | 0.953 |
V |
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O8-H18 | H3 | 0.960 | 1.226 | 1.565 | 2.366 | 3.116 |
H3 |
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O9-H19 | V | 0.960 | 0.957 | 0.952 | 0.953 | 0.953 |
V |
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C4-O10 | V | 1.430 | 1.408 | 1.367 | 1.412 | 1.373 |
L1 |
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O10-H20 | H1 | 0.960 | 0.973 | 0.988 | 0.989 | 1.002 |
H1 |
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aSee Table
Charge density [a.u] at particular atoms of the α- and β-D-glucose molecules depending on
Atom | Flux density [ |
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---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1.0 | 10 | 100 | |
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O10 | H2 | -0.742 | -0.733 | -0.717 | -0.695 | -0.527 |
H1 | - |
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H15 | H2 | 0.177 | 0.170 | 0.179 | 0.190 | 0.237 |
V |
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H16 | L3 | 0.172 | 0.145 | 0.021 | -0.145 | -0.506 |
L3 |
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H17 | V | 0.399 | 0.396 | 0.397 | 0.398 | 0.411 |
V |
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H18 | V | 0.397 | 0.387 | 0.393 | 0.391 | 0.399 |
V |
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H19 | L2 | 0.423 | 0.427 | 0.414 | 0.396 | 0.291 |
V |
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H20 | H1 | 0.412 | 0.415 | 0.421 | 0.429 | 0.456 |
H1 |
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aSee Table
Simplified visualisation of the effect of
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
Bond | Flux density [ |
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---|---|---|---|---|---|---|
Tendency | 0 | 0.1 | 1 | 10 | 100 | |
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O7-H17 | V | 0.960 | 1.037 | 0.966 | 1.031 | 0.972 |
V |
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O8-H18 | V | 0.960 | 1.101 | 1.080 | 1.185 | 1.187 |
IH |
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O9-H19 | H2 | 0.960 | 1.053 | 1.171 | 1.246 | 1.579 |
IH |
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C5-O10 | IL | 1.411 | 1.401 | 1.401 | 1.385 | 1.339 |
V |
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O10-H20 | V | 0.960 | 0.953 | 0.967 | 0.957 | 1.004 |
V |
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C5-H15 | H3 | 1.090 | 1.284 | 1.681 | 2.068 | 3.362 |
H3 |
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C5-H16 | V | 1.091 | 1.154 | 1.112 | 1.123 | 1.088 |
V |
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aSee Table
Simplified visualisation of the effect of
Comparison of the relevant data for D-xylopyranoses and D-xylofuranoses revealed that pyranose anomers metabolise more readily.
The
Performed numerical simulations showed the specific influence of static magnetic field (
D-Glucose in
D-Galactose in
D-Fructose in
Only insignificant effects evoked by