Glycoconjugate Journal

, Volume 10, Issue 3, pp 227–234 | Cite as

Synthetic glycosylation of peptides using unprotected saccharide β-glycosylamines

  • Simon Y. C. Wong
  • Geoffrey R. Guile
  • Thomas W. Rademacher
  • Raymond A. Dwek
Papers

Abstract

Glycopeptides can be valuable tools in determining the influence of carbohydrate moieties on the intrinsic properties of glycoproteins. However, glycopeptides of sufficient quantity and purity are as yet not readily available from biological sources. The chemical coupling of a β-glycosylamino group of an unprotected carbohydrate with an activated aspartic acid residue of an unprotected peptide is a simple method for synthesizing asparagine-linked glycopeptides. In this report we demonstrate that the use of this method is not restricted to β-glycosylamines of simple monosaccharides or short aspartic acid-containing pentapeptides. This is illustrated by the syntheses of several glycopentapeptides containingN,N′-diacetylchitobiose, a glutamine-linked glycopentapeptide containing a biantennary complex oligosaccharide, and glycosylated variants of two analogs of a polypeptide hormone, atriopeptin, containingN,N′-diacetylchitobiose.

Keywords

carbohydrate attachment peptide hormone 

Abbreviations

Ac

acetyl

Bzl

benzyl

DMF

dimethylformamide

Fmoc

9-fluorenylmethoxycarbonyl

Fuc

fucose

Gal

galactose

GlcNAc

N-acetylglucosamine

HBTU

O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluroniumhexa-fluorophosphate

HOBt

1-hydroxybenzotriazole

Man

mannose

m/z

mass/charge

NMR

nuclear magnetic resonance

Xyl

xylose

Z

benzyloxycarbonyl; unless otherwise specified, amino acids are abbreviated using their one-letter codes.

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Copyright information

© Chapman & Hall 1993

Authors and Affiliations

  • Simon Y. C. Wong
    • 1
  • Geoffrey R. Guile
    • 1
  • Thomas W. Rademacher
    • 1
  • Raymond A. Dwek
    • 1
  1. 1.Glycobiology Institute, Department of BiochemistryUniversity of OxfordOxfordUK

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