NDLI: Conformation analysis of d-glucaric acid in deuterium oxide by NMR based on its $J_{HH}$ and $J_{CH}$ coupling constants

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Conformation analysis of d-glucaric acid in deuterium oxide by NMR based on its $J_{HH}$ and $J_{CH}$ coupling constants

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Conformation analysis of d-glucaric acid in deuterium oxide by NMR based on its $J_{HH}$ and $J_{CH}$ coupling constants

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Enomoto-Rogers, Yukiko Masaki, Hisaharu Ito, Tetsuya Furihata, Kazuo Iwata, Tadahisa
Description	Country affiliation: Japan Author Affiliation: Enomoto-Rogers Y ( Science of Polymeric Materials, Department of Biomaterial Sciences, Graduate School of Agricultural Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo, 113-8657, Japan.); Masaki H ( Ensuiko Sugar Refining Co., Ltd, 1-1-1, Fukuura, Kanazawa-ku, Yokohama, Kanagawa, 236-0004, Japan.); Ito T ( Ensuiko Sugar Refining Co., Ltd, 1-1-1, Fukuura, Kanazawa-ku, Yokohama, Kanagawa, 236-0004, Japan.); Furihata K ( Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1, Yayoi, Bunkyo-ku, Tokyo, 113-8657, Japan.); Iwata T ( Science of Polymeric Materials, Department of Biomaterial Sciences, Graduate School of Agricultural Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo, 113-8657, Japan.)
Abstract	d-Glucaric acid (GA) is an aldaric acid and consists of an asymmetric acyclic sugar backbone with a carboxyl group positioned at either end of its structure (i.e., the C1 and C6 positions). The purpose of this study was to conduct a conformation analysis of flexible GA as a solution in deuterium oxide by NMR spectroscopy, based on J-resolved conformation analysis using proton–proton $(^{3}J_{HH})$ and proton–carbon $(^{2}J_{CH}$ and $^{3}J_{CH})$ coupling constants, as well as nuclear overhauser effect spectroscopy (NOESY). The $^{2}J_{CH}$ and $^{3}J_{CH}$ coupling constants were measured using the J-resolved heteronuclear multiple bond correlation (HMBC) NMR technique. NOESY correlation experiments indicated that H2 and H5 were in close proximity, despite the fact that these protons were separated by too large distance in the fully extended form of the chain structure to provide a NOESY correlation. The validities of the three possible conformers along the three different bonds (i.e., C2C3, C3C4, and C4C5) were evaluated sequentially based on the J-coupling values and the NOESY correlations. The results of these analyses suggested that there were three dominant conformers of GA, including conformer 1, which was H2H3:gauche, H3H4:anti, and H4H5:gauche; conformer 2, which was H2H3:gauche, H3H4:anti, and H4H5:anti; and conformer 3, which was H2H3:gauche, H3H4: gauche, and H4H5:anti. These results also suggested that all three of these conformers exist in equilibrium with each other. Lastly, the results of the current study suggested that the conformational structures of GA in solution were ‘bent’ rather than being fully extended. Copyright © 2016 John Wiley & Sons, Ltd.
File Format	HTM / HTML
ISSN	07491581
Issue Number	7
Journal	Magnetic Resonance in Chemistry
Volume Number	54
e-ISSN	1097458X
Language	English
Publisher	Wiley Heyden
Publisher Date	2016-07-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Materials Science

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