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Synthesis 2007(17): 2647-2652  
DOI: 10.1055/s-2007-983813
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Triazole-Linked Manno- and Glucopyranosyl Amino Acids

Janaína V. dos Anjosa,b, Denis Sinou*a, Sebastiao J. de Meloc, Rajendra M. Srivastava*b
a Laboratoire de Synthèse Asymétrique, UMR 5246-ICBMS, CPE Lyon, Université Claude Bernard Lyon1, 43 boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France
Fax: +33(4)78898914; e-Mail: sinou@univ-lyon1.fr;
b Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50740-540 Recife, PE, Brazil
Fax: +55(81)21268442; e-Mail: rms@ufpe.br;
c Departamento de Antibióticos, Universidade Federal de Pernambuco, Cidade Universitária, 50670-901 Recife, PE, Brazil
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Publication History

Received 15 May 2007
Publication Date:
24 July 2007 (online)

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Abstract

The synthesis of two types of triazole-linked glycosyl amino acids, at C-4 and at the anomeric position for mannopyranose and glucopyranose derivatives, respectively, via a copper-catalyzed [3+2] cycloaddition of acetylenic amino acid derivatives and azide-containing glycoside is described.

Key words

[3+2] cycloaddition - acetylenic amino acid - azidocarbohydrate - triazole - glycosyl amino acids