Xue, Yan
- Department of Molecular Sciences, Swedish University of Agricultural Sciences
Research article2022Peer reviewedOpen access
Determination of Amide cis/trans Isomers in N-Acetyl-d-glucosamine: Tailored NMR Analysis of the N-Acetyl Group Conformation
Xue, Yan; Nestor, Gustav
Abstract
N-Acetyl-d-glucosamine (GlcNAc) is one of the most common amino sugars in nature, but the conformation of its N-acetyl group has drawn little attention. We report herein the first identification of NH protons of the amide cis forms of alpha- and beta-GlcNAc by NMR spectroscopy. Relative quantification and thermodynamic analysis of both cis and trans forms was carried out in aqueous solution. The NH protons were further utilized by adapting protein NMR experiments to measure eight J-couplings within the N-acetyl group, of which six are sensitive to the H2-NH conformation and two are sensitive to the amide conformation. For amide cis and trans forms, the orientation between H2 and NH was determined as anti conformation, while a small percentage of syn conformation was predicted for the amide trans form of beta-GlcNAc. This approach holds great promise for the detailed conformational analysis of GlcNAc in larger biomolecules, such as glycoproteins and polysaccharides.
Keywords
conformational analysis; isotopic labelling; N-acetylglucosamine; NMR spectroscopy
Published in
ChemBioChem
2022, volume: 23, number: 17, article number: e202200338
Publisher: WILEY-V C H VERLAG GMBH
SLU Authors
Nestor, Gustav
- Department of Molecular Sciences, Swedish University of Agricultural Sciences
- Department of Molecular Sciences, Swedish University of Agricultural Sciences
UKÄ Subject classification
Biochemistry and Molecular Biology
Publication identifier
- DOI: https://doi.org/10.1002/cbic.202200338
Permanent link to this page (URI)
https://res.slu.se/id/publ/118349