Jump to main content
Jump to site search

Issue 16, 2007
Previous Article Next Article

Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins

Author affiliations

Abstract

This study describes the synthesis of the α- and β-linked N-acetyllactosamine (Galp-β-1,4-GlcNAc; LacNAc) glycosides of threonine (LacNAc-Thr). LacNAc-α-Thr was prepared by direct chemical coupling of a 2-azido-2-deoxy-lactose disaccharide donor to a suitable partially protected threonine unit. In contrast, stepwise chemical generation of β-linked N-acetylglucosamine followed by enzymatic galactosylation to give LacNAc-β-Thr proved effective, whereas use of a 2-azido-2-deoxy-lactose donor in acetonitrile failed to give the desired β-linked disaccharyl glycoside. This study illustrates that it is possible to overcome the inherent stereoselection for 1,2-trans chemical glycosylation with a GlcNAc donor, and that the well-established preference of bovine β-1,4-galactosyltransferase for β-linked acceptor substrates can also be overcome. Using this knowledge, short glycopeptide fragments based on T. cruzi mucin sequences, Thr-Thr-[LacNAcThr]-Thr-Thr-Gly, were synthesised. All LacNAc-based compounds outlined were shown to serve as acceptor substrates for sialylation by T. cruzi trans-sialidase.

Graphical abstract: Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins

Back to tab navigation

Publication details

The article was received on 23 May 2007, accepted on 29 Jun 2007 and first published on 16 Jul 2007


Article type: Paper
DOI: 10.1039/B707772F
Citation: Org. Biomol. Chem., 2007,5, 2645-2657
  •   Request permissions

    Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins

    V. L. Campo, I. Carvalho, S. Allman, B. G. Davis and R. A. Field, Org. Biomol. Chem., 2007, 5, 2645
    DOI: 10.1039/B707772F

Search articles by author

Spotlight

Advertisements