Theoretical Studies on the Electronic Structure Parameters and Reactive Activity of Neu5Gc and Neu5Ac under Food Processing Solvent Environment
Abstract
:1. Introduction
2. Computational Details
2.1. Molecular Structure Parameters Calculation
2.2. Antioxidant Mechanism
3. Results and Discussion
3.1. Molecular Structure and Electrostatic Potential
3.2. Frontier Molecular Orbital and Natural Bond Orbital
3.3. Intramolecular Hydrogen Bonds
3.4. IGM Analysis of Intramolecular Hydrogen Bonds
3.5. Molecular Reactivity Index
3.6. Molecular Condensed Fukui Function
3.7. Antioxidation Mechanism of Neu5Ac and Neu5Gc
3.7.1. Hydrogen Atom Transfer Mechanism (HAT)
3.7.2. Single Electron Transfer Mechanism (SET)
3.7.3. Single-electron Transfer Followed by Proton Transfer Mechanism (SET-PT)
3.7.4. Sequential Proton Loss Electron Transfer Mechanism (SPLET)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Neu5Gc | Bond | ρ | ▽2ρ | V | G | HBCP | EHB | Length | Angle |
---|---|---|---|---|---|---|---|---|---|
Gas | O2–H31...O9 | 0.02953 | 0.1126 | −0.02557 | 0.02687 | 0.001301 | −33.56 | 2.794 | 4.804 |
O3–H34...O1 | 0.02885 | 0.1327 | –0.02784 | 0.03050 | 0.002673 | −36.55 | 2.524 | 6.080 | |
O10–H41...O9 | 0.02385 | 0.1051 | –0.02086 | 0.02357 | 0.002710 | –27.39 | 2.646 | 13.65 | |
N11–H30...O5 | 0.02255 | 0.09263 | –0.01774 | 0.02045 | 0.002705 | –23.29 | 2.921 | 2.811 | |
Acetic acid | O10–H41...O9 | 0.2266 | 0.1019 | –0.01975 | 0.2262 | 0.002869 | –25.94 | 2.653 | 4.951 |
Benzene | O10–H41...O9 | 0.02319 | 0.1038 | –0.02031 | 0.02313 | 0.002817 | –26.67 | 2.652 | 5.516 |
Gas | O3–H33...O1 | 0.02262 | 0.1058 | –0.02053 | 0.02349 | 0.002964 | –26.95 | 2.586 | 8.897 |
O2–H30...O9 | 0.02907 | 0.1101 | –0.02485 | 0.02619 | 0.001343 | –32.62 | 2.800 | 4.906 | |
Acetic acid | O2–H30...O9 | 0.02361 | 0.08990 | –0.01891 | 0.02069 | 0.001782 | –24.82 | 2.850 | 5.233 |
Benzene | O3–H33...O1 | 0.02027 | 0.09740 | –0.01829 | 0.02132 | 0.003026 | –24.02 | 2.625 | 11.40 |
O2–H30...O9 | 0.02818 | 0.1064 | –0.02373 | 0.02518 | 0.001443 | –31.16 | 2.816 | 4.511 |
Neu5Gc | ||||||||
---|---|---|---|---|---|---|---|---|
Media | HOMO | LUMO | Egap | η | s | χ | μ | ω |
Gas | −8.900 | 0.753 | 9.653 | 4.826 | 0.1036 | 4.074 | −4.074 | 1.719 |
Benzene | −8.867 | 0.955 | 9.822 | 4.911 | 0.1018 | 3.955 | −3.955 | 1.593 |
Ethanol | −8.660 | 1.039 | 9.699 | 4.849 | 0.1030 | 3.810 | −3.810 | 1.496 |
Acetic acid | −8.728 | 0.995 | 9.723 | 4.861 | 0.1028 | 3.866 | −3.866 | 1.537 |
Lactic acid | −8.715 | 1.125 | 9.840 | 4.920 | 0.1016 | 3.795 | −3.795 | 1.463 |
Formic acid | −8.720 | 1.013 | 9.733 | 4.866 | 0.1027 | 3.853 | −3.853 | 1.525 |
Water | −8.731 | 0.988 | 9.720 | 4.860 | 0.1028 | 3.871 | −3.871 | 1.542 |
Neu5Ac | ||||||||
Gas | −8.766 | 0.878 | 9.644 | 4.822 | 0.1036 | 3.944 | −3.944 | 1.613 |
Benzene | −8.674 | 1.027 | 9.702 | 4.851 | 0.1030 | 3.823 | −3.823 | 1.506 |
Ethanol | −8.594 | 1.068 | 9.662 | 4.831 | 0.1034 | 3.762 | −3.762 | 1.465 |
Acetic acid | −8.701 | 1.021 | 9.722 | 4.860 | 0.1028 | 3.840 | −3.840 | 1.516 |
Lactic acid | −8.578 | 1.141 | 9.719 | 4.859 | 0.1029 | 3.719 | −3.718 | 1.423 |
Formic acid | −8.548 | 1.030 | 9.578 | 4.789 | 0.1043 | 3.759 | −3.759 | 1.475 |
Water | −8.718 | 1.007 | 9.726 | 4.863 | 0.1028 | 3.855 | −3.855 | 1.528 |
f − | Electrophilic Activity of Neu5Gc | ||||||
---|---|---|---|---|---|---|---|
Media | O2 | O3 | O4 | O5 | O6 | O7 | O10 |
Gas | 0.1237 | 0.02612 | 0.01854 | −0.003166 | 0.01067 | 0.009959 | 0.05184 |
Benzene | 0.08462 | 0.01581 | 0.01468 | 0.001390 | 0.008207 | 0.007863 | 0.04109 |
Acetic acid | 0.06119 | 0.01006 | 0.008661 | 0.002425 | 0.005481 | 0.004638 | 0.03003 |
Ethanol | 0.03166 | 0.01348 | 0.008483 | 0.004389 | 0.004433 | 0.003873 | 0.02739 |
Formic acid | 0.02883 | 0.01327 | 0.008223 | 0.004598 | 0.003941 | 0.003317 | 0.02415 |
Lactic acid | 0.05031 | 0.009583 | 0.007909 | 0.002491 | 0.004599 | 0.003322 | 0.03325 |
Water | 0.03077 | 0.01305 | 0.008335 | 0.004534 | 0.003866 | 0.003205 | 0.02450 |
f + | Nucleophilic Activity of Neu5Gc | ||||||
Gas | 0.02046 | 0.01737 | 0.04551 | 0.001062 | 0.0694 | 0.01091 | 0.01983 |
Benzene | 0.01696 | 0.01141 | 0.05685 | 0.002364 | 0.09615 | 0.003067 | 0.007161 |
Acetic acid | 0.01556 | 0.006019 | 0.04722 | 0.001904 | 0.1224 | 0.001077 | 0.002703 |
Ethanol | 0.01396 | 0.004336 | 0.04283 | 0.001304 | 0.1240 | 0.0006920 | 0.001186 |
Formic acid | 0.01279 | 0.003578 | 0.04548 | 0.001167 | 0.1269 | 0.0005470 | 0.0008410 |
Lactic acid | 0.01419 | 0.007517 | 0.04970 | 0.001725 | 0.1086 | 0.001256 | 0.001962 |
Water | 0.01274 | 0.003522 | 0.04491 | 0.001134 | 0.1270 | 0.0005410 | 0.0007780 |
f − | Electrophilic Activity of Neu5Ac | |||||
---|---|---|---|---|---|---|
Media | O2 | O3 | O4 | O5 | O6 | O7 |
Gas | 0.1140 | 0.02236 | 0.01776 | 0.0001650 | 0.01092 | 0.01185 |
Benzene | 0.06632 | 0.01300 | 0.009534 | 0.0005200 | 0.007312 | 0.007243 |
Acetic acid | 0.05073 | 0.009047 | 0.008116 | 0.001855 | 0.005053 | 0.004259 |
Ethanol | 0.02826 | 0.01184 | 0.007726 | 0.003867 | 0.004107 | 0.003490 |
Formic acid | 0.05069 | 0.008504 | 0.007130 | 0.003015 | 0.003647 | 0.002429 |
Lactic acid | 0.05070 | 0.009064 | 0.007035 | 0.002215 | 0.004367 | 0.003040 |
Water | 0.04718 | 0.008686 | 0.007317 | 0.003156 | 0.003574 | 0.002371 |
f + | Nucleophilic Activity of Neu5Ac | |||||
Gas | 0.02053 | 0.01515 | 0.05226 | 0.001968 | 0.08011 | 0.006588 |
Benzene | 0.01705 | 0.01137 | 0.05745 | 0.002491 | 0.09739 | 0.003006 |
Acetic acid | 0.01432 | 0.006090 | 0.04783 | 0.002124 | 0.1225 | 0.001194 |
Ethanol | 0.01363 | 0.004200 | 0.04485 | 0.001290 | 0.1236 | 0.0006360 |
Formic acid | 0.01236 | 0.003406 | 0.04676 | 0.001115 | 0.1266 | 0.0005200 |
Lactic acid | 0.01399 | 0.007559 | 0.05077 | 0.001706 | 0.1076 | 0.001251 |
Water | 0.01237 | 0.003225 | 0.04587 | 0.001147 | 0.1267 | 0.0005170 |
HAT | BDE of Neu5Gc | ||||||
---|---|---|---|---|---|---|---|
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H | O10-H |
Gas | 104.78 | 108.41 | 104.14 | 108.24 | 114.22 | 103.51 | 108.98 |
Benzene | 104.78 | 109.22 | 105.93 | 108.81 | 115.21 | 104.79 | 109.30 |
Acetic acid | 108.56 | 109.89 | 108.24 | 109.72 | 118.61 | 106.76 | 109.51 |
Ethanol | 107.86 | 108.75 | 108.10 | 108.36 | 117.94 | 106.04 | 107.98 |
Formic acid | 109.37 | 109.86 | 110.17 | 110.40 | 116.21 | 108.08 | 109.40 |
Lactic acid | 106.73 | 107.93 | 105.98 | 107.60 | 114.60 | 104.55 | 107.64 |
Water | 105.77 | 106.59 | 106.16 | 106.09 | 118.10 | 104.03 | 105.25 |
PDE of Neu5Gc | |||||||
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H | O10-H |
Gas | 218.48 | 222.10 | 217.84 | 221.93 | 227.91 | 217.21 | 222.67 |
Benzene | 24.55 | 28.98 | 25.70 | 28.58 | 34.98 | 24.56 | 29.06 |
Acetic acid | 9.60 | 10.94 | 9.29 | 10.76 | 19.65 | 7.80 | 10.55 |
Ethanol | 7.47 | 8.35 | 7.70 | 7.96 | 17.55 | 5.65 | 7.59 |
Formic acid | 13.01 | 13.51 | 13.82 | 14.05 | 19.86 | 11.73 | 13.05 |
Lactic acid | 18.35 | 19.55 | 17.60 | 19.22 | 26.22 | 16.17 | 19.26 |
Water | 9.78 | 10.60 | 10.17 | 10.10 | 22.11 | 8.04 | 9.26 |
PA of Neu5Gc | |||||||
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H | O10-H |
Gas | 349.69 | 335.18 | 337.41 | 321.84 | 317.18 | 322.18 | 366.36 |
Benzene | 115.46 | 119.74 | 101.89 | 95.90 | 80.55 | 90.27 | 124.17 |
Acetic acid | 63.65 | 67.18 | 53.90 | 54.12 | 34.16 | 62.87 | 66.19 |
Ethanol | 49.60 | 51.33 | 39.32 | 52.78 | 20.34 | 50.54 | 54.36 |
Formic acid | 50.97 | 52.44 | 42.04 | 54.02 | 24.23 | 53.13 | 52.79 |
Lactic acid | 75.79 | 77.98 | 63.25 | 59.65 | 40.95 | 71.48 | 79.43 |
Water | 47.40 | 48.75 | 37.94 | 49.74 | 23.80 | 49.78 | 48.86 |
ETE of Neu5Gc | |||||||
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H | O10-H |
Gas | 59.60 | 87.74 | 81.24 | 100.90 | 111.54 | 95.84 | 57.12 |
Benzene | 81.85 | 91.99 | 96.56 | 105.43 | 127.18 | 107.04 | 77.65 |
Acetic acid | 83.46 | 81.26 | 92.89 | 94.15 | 123.00 | 82.44 | 79.87 |
Ethanol | 97.84 | 97.00 | 108.36 | 95.15 | 137.17 | 95.08 | 93.19 |
Formic acid | 96.61 | 95.64 | 106.35 | 94.60 | 130.20 | 93.17 | 94.83 |
Lactic acid | 82.39 | 81.41 | 94.19 | 99.41 | 125.11 | 84.53 | 79.67 |
Water | 96.37 | 95.84 | 106.22 | 94.35 | 132.30 | 92.25 | 94.39 |
HAT | BDE of Neu5Ac | |||||
---|---|---|---|---|---|---|
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H |
Gas | 108.40 | 108.26 | 104.24 | 108.14 | 113.67 | 103.38 |
Benzene | 109.13 | 109.20 | 105.84 | 108.85 | 114.97 | 104.85 |
Acetic acid | 109.41 | 109.24 | 108.42 | 110.01 | 118.39 | 107.14 |
Ethanol | 107.93 | 108.57 | 108.09 | 108.45 | 118.04 | 106.18 |
Formic acid | 108.52 | 109.09 | 109.32 | 109.74 | 114.48 | 107.42 |
Lactic acid | 107.70 | 107.86 | 105.88 | 107.66 | 114.56 | 104.57 |
Water | 105.33 | 105.92 | 105.65 | 105.38 | 112.17 | 107.94 |
PDE of Neu5Ac | ||||||
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H |
Gas | 224.53 | 224.39 | 220.37 | 224.27 | 229.80 | 219.51 |
Benzene | 33.07 | 33.13 | 29.78 | 32.78 | 38.90 | 28.79 |
Acetic acid | 12.24 | 12.06 | 11.25 | 12.84 | 21.22 | 9.97 |
Ethanol | 9.10 | 9.74 | 9.25 | 9.62 | 19.21 | 7.35 |
Formic acid | 14.68 | 15.25 | 15.48 | 15.89 | 20.63 | 13.57 |
Lactic acid | 22.60 | 22.76 | 20.78 | 22.56 | 29.45 | 19.47 |
Water | 11.71 | 12.29 | 12.02 | 11.76 | 18.30 | 14.32 |
PA of Neu5Ac | ||||||
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H |
Gas | 354.54 | 342.11 | 340.61 | 327.11 | 319.68 | 327.11 |
benzene | 117.94 | 121.75 | 103.89 | 100.18 | 81.95 | 94.44 |
Acetic acid | 65.75 | 68.15 | 53.78 | 69.30 | 35.28 | 65.96 |
Ethanol | 50.07 | 51.18 | 39.54 | 52.67 | 20.76 | 50.83 |
Formic acid | 50.67 | 51.98 | 41.52 | 53.51 | 23.54 | 52.55 |
Lactic acid | 77.73 | 78.55 | 64.91 | 63.05 | 48.85 | 73.14 |
water | 49.79 | 48.11 | 38.00 | 49.49 | 23.82 | 48.58 |
ETE of Neu5Ac | ||||||
Bond | O2-H | O3-H | O4-H | O5-H | O6-H | O7-H |
Gas | 68.37 | 80.65 | 78.13 | 95.53 | 108.49 | 90.78 |
Benzene | 83.71 | 79.96 | 94.46 | 101.18 | 125.53 | 102.93 |
Acetic acid | 82.21 | 79.63 | 93.19 | 79.26 | 121.66 | 79.73 |
Ethanol | 97.44 | 96.96 | 108.12 | 95.35 | 137.09 | 94.93 |
Formic acid | 96.06 | 95.32 | 106.01 | 96.44 | 129.15 | 93.08 |
Lactic acid | 81.43 | 80.77 | 92.43 | 96.06 | 117.16 | 82.88 |
Water | 93.54 | 95.80 | 105.65 | 93.89 | 126.11 | 97.36 |
IP | Gas | Benzene | Acetic Acid | Ethanol | Formic Acid | Lactic Acid | Water |
---|---|---|---|---|---|---|---|
Neu5Ac | 198.37 | 168.58 | 135.72 | 138.41 | 132.06 | 136.56 | 131.63 |
Neu5Gc | 200.81 | 172.75 | 137.51 | 139.97 | 134.57 | 139.84 | 133.99 |
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Chang, R.; Yang, B.; Zhu, Q.-J. Theoretical Studies on the Electronic Structure Parameters and Reactive Activity of Neu5Gc and Neu5Ac under Food Processing Solvent Environment. Molecules 2019, 24, 313. https://doi.org/10.3390/molecules24020313
Chang R, Yang B, Zhu Q-J. Theoretical Studies on the Electronic Structure Parameters and Reactive Activity of Neu5Gc and Neu5Ac under Food Processing Solvent Environment. Molecules. 2019; 24(2):313. https://doi.org/10.3390/molecules24020313
Chicago/Turabian StyleChang, Rui, Bowen Yang, and Qiu-Jin Zhu. 2019. "Theoretical Studies on the Electronic Structure Parameters and Reactive Activity of Neu5Gc and Neu5Ac under Food Processing Solvent Environment" Molecules 24, no. 2: 313. https://doi.org/10.3390/molecules24020313