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Crystal structure and solution conformation of 1‐ N ‐acetyl‐β‐ D ‐glucopyranosyl amine: A model for the glycopeptide linkage
Author(s) -
Bush C. Allen,
Blumberg Karl,
Brown Joe N.
Publication year - 1982
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360211004
Subject(s) - chemistry , amide , glycosyl , ring (chemistry) , crystal structure , stereochemistry , pyranose , crystallography , amine gas treating , asparagine , aqueous solution , hydrogen bond , molecule , amino acid , organic chemistry , biochemistry
The crystal structure of the title compound, a model for the glycosyl linkage between the asparagine side chain and N ‐acetyl glucosamine in glycoproteins, has been determined and compared to other model structures. The pyranose ring in the crystal is in the 4 C 1 chair conformation and the amide functions at C 1 and at C 2 are both oriented such that the amide protons are nearly trans to their respective sugar‐ring protons. Coupling constants determined from the fully assigned proton nmr spectrum in aqueous solution are consistent with the conformation in the crystal.