𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Crystal structure and solution conformation of 1-N-acetyl-β-D-glucopyranosyl amine: A model for the glycopeptide linkage

✍ Scribed by C. Allen Bush; Karl Blumberg; Joe N. Brown


Publisher
Wiley (John Wiley & Sons)
Year
1982
Tongue
English
Weight
315 KB
Volume
21
Category
Article
ISSN
0006-3525

No coin nor oath required. For personal study only.

✦ Synopsis


Abstract

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.