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Article

1H-NMR Karplus Analysis of Molecular Conformations of Glycerol under Different Solvent Conditions: A Consistent Rotational Isomerism in the Backbone Governed by Glycerol/Water Interactions

by
Yoshihiro Nishida
1,*,
Reina Aono
1,
Hirofumi Dohi
1,
Wuxiao Ding
2 and
Hirotaka Uzawa
2
1
Molecular Chirality Research Center, Department of Applied Biological Chemistry, Institute of Environmental Horticulture, Chiba University, Matsudo 271-8510, Japan
2
Nanomaterials Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba 305-8565, Japan
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2023, 24(3), 2766; https://doi.org/10.3390/ijms24032766
Submission received: 9 January 2023 / Revised: 23 January 2023 / Accepted: 25 January 2023 / Published: 1 February 2023
(This article belongs to the Special Issue 25th Anniversary of IJMS: Advances in Biochemistry)
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Abstract

Glycerol is a symmetrical, small biomolecule with high flexibility in molecular conformations. Using a 1H-NMR spectroscopic Karplus analysis in our way, we analyzed a rotational isomerism in the glycero backbone which generates three kinds of staggered conformers, namely gt (gauche-trans), gg (gauche-gauche), and tg (trans-gauche), at each of sn-1,2 and sn-2,3 positions. The Karplus analysis has disclosed that the three rotamers are consistently equilibrated in water keeping the relation of ‘gt:gg:tg = 50:30:20 (%)’ at a wide range of concentrations (5 mM~540 mM). The observed relation means that glycerol in water favors those symmetric conformers placing 1,2,3-triol groups in a gauche/gauche geometry. We have found also that the rotational isomerism is remarkably changed when the solvent is replaced with DMSO-d6 or dimethylformamide (DMF-d7). In these solvents, glycerol gives a relation of ‘gt:gg:tg = 40:30:30 (%)’, which means that a remarkable shift occurs in the equilibrium between gt and tg conformers. By this shift, glycerol turns to also take non-symmetric conformers orienting one of the two vicinal diols in an antiperiplanar geometry.
Keywords: glycerol; rotational isomerism; conformation; Karplus equation; 1H NMR spectroscopy; bilateral symmetry; cell membrane; glycerolipids glycerol; rotational isomerism; conformation; Karplus equation; 1H NMR spectroscopy; bilateral symmetry; cell membrane; glycerolipids
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MDPI and ACS Style

Nishida, Y.; Aono, R.; Dohi, H.; Ding, W.; Uzawa, H. 1H-NMR Karplus Analysis of Molecular Conformations of Glycerol under Different Solvent Conditions: A Consistent Rotational Isomerism in the Backbone Governed by Glycerol/Water Interactions. Int. J. Mol. Sci. 2023, 24, 2766. https://doi.org/10.3390/ijms24032766

AMA Style

Nishida Y, Aono R, Dohi H, Ding W, Uzawa H. 1H-NMR Karplus Analysis of Molecular Conformations of Glycerol under Different Solvent Conditions: A Consistent Rotational Isomerism in the Backbone Governed by Glycerol/Water Interactions. International Journal of Molecular Sciences. 2023; 24(3):2766. https://doi.org/10.3390/ijms24032766

Chicago/Turabian Style

Nishida, Yoshihiro, Reina Aono, Hirofumi Dohi, Wuxiao Ding, and Hirotaka Uzawa. 2023. "1H-NMR Karplus Analysis of Molecular Conformations of Glycerol under Different Solvent Conditions: A Consistent Rotational Isomerism in the Backbone Governed by Glycerol/Water Interactions" International Journal of Molecular Sciences 24, no. 3: 2766. https://doi.org/10.3390/ijms24032766

APA Style

Nishida, Y., Aono, R., Dohi, H., Ding, W., & Uzawa, H. (2023). 1H-NMR Karplus Analysis of Molecular Conformations of Glycerol under Different Solvent Conditions: A Consistent Rotational Isomerism in the Backbone Governed by Glycerol/Water Interactions. International Journal of Molecular Sciences, 24(3), 2766. https://doi.org/10.3390/ijms24032766

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