Conformational Distributions of Phenyl β-D-Glucopyranoside and Gastrodin in Solution by Vibrational Optical Activity and Theoretical Calculations
Abstract
:1. Introduction
2. Results and Discussion
2.1. Low-Energy Conformers of Phenyl β-D-Glucopyranoside and Gastrodin
2.2. Experimental and Simulated IR and VCD Spectra of ph-β-Glu and Gastrodin
2.3. Experimental and Simulated Raman and ROA Spectra of ph-β-Glu and Gastrodin in Water
2.4. Some General Comments about the Conformational Distribution of ph-β-Glu and Gastrodin in DMSO and in Water
3. Materials and Methods
3.1. Experimental
3.2. Theoretical
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Structural Parameters | G-g+/cc/T | G+g-/cc/T | Tg+/cc/T | G-g-/cc/T |
---|---|---|---|---|
r(H2-O1)/Å | 2.583 | 2.590 | 2.583 | 2.582 |
r(H3-O2)/Å | 2.528 | 2.540 | 2.551 | 2.542 |
r(H4-O3)/Å | 2.426 | 2.420 | 2.471 | 2.419 |
r(H6-O4/O5)/Å | 2.423 | 2.407 | 1.994 | 3.060 |
θ(C2-C1-O1-C7)/° | 160.1 | 161.2 | 160.0 | 160.1 |
θ(C3-C2-O2-H2)/° | −172.4 | −172.3 | −172.2 | −172.5 |
θ(C4-C3-O3-H3)/° | 176.8 | 175.8 | 176.3 | 176.6 |
θ(C5-C4-O4-H4)/° | 173.3 | 171.9 | 179.3 | 172.5 |
θ(O5-C5-C6-O6)/° | −60.2 | 61.6 | 169.7 | −66.5 |
θ(C5-C6-O6-H6)/° | 57.2 | −56.6 | 48.2 | −82.1 |
θ(C1-O1-C7-C12)/° | 14.8 | 12.6 | 14.8 | 14.4 |
Structural Parameters | G-g+/cc/T/G+g- | G+g-/cc/T/G-g- | G+g-/cc/T/G+g+ | G+g-/cc/T/G-g+ |
---|---|---|---|---|
r(H2-O1)/Å | 2.596 | 2.595 | 2.596 | 2.593 |
r(H3-O2)/Å | 2.531 | 2.529 | 2.532 | 2.531 |
r(H4-O3)/Å | 2.409 | 2.412 | 2.409 | 2.411 |
r(H6-O5)/Å | 2.405 | 2.400 | 2.403 | 2.401 |
r(H12-O5)/Å | 2.553 | 2.558 | 2.556 | 2.550 |
θ(C2-C1-O1-C7)/° | 161.6 | 161.5 | 161.6 | 161.1 |
θ(C3-C2-O2-H2)/° | −171.6 | −171.6 | −171.6 | −171.7 |
θ(C4-C3-O3-H3)/° | 176.2 | 176.4 | 176.2 | 176.2 |
θ(C5-C4-O4-H4)/° | 171.2 | 171.4 | 171.2 | 171.4 |
θ(O5-C5-C6-O6)/° | −60.2 | 61.4 | 61.4 | 61.4 |
θ(C5-C6-O6-H6)/° | 57.4 | −57.1 | −57.3 | −57.2 |
θ(C1-O1-C7-C12)/° | 12.5 | 12.7 | 12.5 | 13.3 |
θ(C9-C10-C13-O7)/° | 101.2 | −73.4 | 74.6 | −100.9 |
θ(C10-C13-O7-H7)/° | −56.4 | −56.4 | 56.4 | 56.7 |
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Alshalalfeh, M.; Sun, N.; Moraes, A.H.; Utani, A.P.A.; Xu, Y. Conformational Distributions of Phenyl β-D-Glucopyranoside and Gastrodin in Solution by Vibrational Optical Activity and Theoretical Calculations. Molecules 2023, 28, 4013. https://doi.org/10.3390/molecules28104013
Alshalalfeh M, Sun N, Moraes AH, Utani APA, Xu Y. Conformational Distributions of Phenyl β-D-Glucopyranoside and Gastrodin in Solution by Vibrational Optical Activity and Theoretical Calculations. Molecules. 2023; 28(10):4013. https://doi.org/10.3390/molecules28104013
Chicago/Turabian StyleAlshalalfeh, Mutasem, Ningjie Sun, Amanda Hanashiro Moraes, Alexandra Paola Aponte Utani, and Yunjie Xu. 2023. "Conformational Distributions of Phenyl β-D-Glucopyranoside and Gastrodin in Solution by Vibrational Optical Activity and Theoretical Calculations" Molecules 28, no. 10: 4013. https://doi.org/10.3390/molecules28104013