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Synthesis of N 4 ‐(2‐acetamido‐2‐deoxy‐β‐ D ‐glucopyranosyl)‐ L ‐asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues
Author(s) -
Malik Jayshri J.,
Risley John M.
Publication year - 2001
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/1097-458x(200102)39:2<98::aid-mrc792>3.0.co;2-3
Subject(s) - chemistry , stereochemistry , methylene , carbon 13 nmr , proton nmr , linkage (software) , medicinal chemistry , biochemistry , gene
Abstract N 4 ‐(2‐Acetamido‐2‐deoxy‐β‐ D ‐glucopyranosyl)‐ L ‐asparagine is the principle linkage in the structure of N‐linked glycoproteins. Complete assignments of the 1 H and 13 C NMR spectra for three analogues of the naturally‐occurring N ‐glycosylic structure were made for N ‐(2‐acetamido‐2‐deoxy‐β‐ D ‐glucopyranosyl)chloroacetamide, N ‐(2‐acetamido‐2‐deoxy‐β‐ D ‐glucopyranosyl)bromoacetamide and N 1 ‐(2‐acetamido‐2‐deoxy‐β‐ D ‐glucopyranosyl)glycinamide. The methylene groups adjacent to the N ‐glycosylic bond are AB spin systems. Copyright © 2001 John Wiley & Sons, Ltd.