Open AccessStructural Studies on 2‐Acetamido‐1‐ N ‐(4‐ l ‐aspartyl)‐ 2‐deoxy‐β‐ d ‐glucopyranosylamine and 2‐Acetamido‐6‐ O ‐(α‐ l ‐fucopyranosyl)‐1‐ N ‐(4‐ l ‐aspartyl)‐2‐deoxy‐β‐ d ‐glucopyranosylamine by 360‐MHz Proton‐Magnetic‐Resonance Spectroscopy
Author(s) -
DORLAND Lambertus,
SCHUT Bernardus L.,
VLIEGENTHART Johannes F. G.,
STRECKER Gérard,
FOURNET Bernard,
SPIK Geneviève,
MONTREUIL Jean
Publication year - 1977
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1111/j.1432-1033.1977.tb11294.x
Subject(s) - chemistry , pyranose , geminal , glycosidic bond , stereochemistry , coupling constant , beta (programming language) , crystallography , nuclear magnetic resonance spectroscopy , nmr spectra database , spectral line , nuclear magnetic resonance , physics , particle physics , computer science , programming language , enzyme , biochemistry , astronomy
The 360‐MHz proton magnetic resonance spectra of 2‐acetamido‐1‐ N ‐(4‐ l ‐aspartyl)‐ 2‐deoxy‐β‐ d ‐glucopyranosylamine (GlcNAcβ1 → Asn) and 2‐acetamido‐6‐ O ‐(α‐ l ‐fucopyranosyl)‐1‐ N ‐(4‐ l ‐aspartyl)‐2‐deoxy‐β‐ d ‐glucopyranosylamine (Fucα1 → 6GlcNAcβ1 → Asn) in deuterium oxide were completely interpreted. The chemical shifts and coupling constants were refined by simulation of the spectra. By means of an adapted Karplus equation the pyranose ring conformation of the sugars was calculated. The change of the geminal coupling constant J 6a,6b in the N ‐acetylglucosamine residue of Fucα1 → 6GlcNAcβ1 → Asn with respect to GlcNAcβ1 → Asn is proposed to be characteristic for the (1 → 6) glycosidic linkage.