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

Abstract:

This study describes the synthesis of the alpha- and beta-linked N-acetyllactosamine (Galp-beta-1,4-GlcNAc; LacNAc) glycosides of threonine (LacNAc-Thr). LacNAc-a-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 beta-linked N-acetylglucosamine followed by enzymatic galactosylation to give LacNAc-beta-Thr proved effective, whereas use of a 2-azido-2-deoxy-l...

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Publication status:
Published

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Publisher copy:
10.1039/b707772f

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry
Volume:
5
Issue:
16
Pages:
2645-2657
Publication date:
2007-08-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:8e5cf1b6-ea50-4a79-a761-cf5c21d28e0c
Source identifiers:
40435
Local pid:
pubs:40435

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