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Synthesis 2006(18): 3146-3152
DOI: 10.1055/s-2006-942509
DOI: 10.1055/s-2006-942509
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Chemoenzymatic Synthesis of Triazole-Linked Glycopeptides
Further Information
Received
29 March 2006
Publication Date:
25 July 2006 (online)
Publication History
Publication Date:
25 July 2006 (online)
Abstract
Triazole-linked glycopeptides are prepared by C-terminal elongation of glycoamino acids with proteinogenic amino acids following a chemical or enzymatic coupling protocol. Two orthogonal routes for a chemoenzymatic strategy were explored, involving a click-reaction before amide bond formation or in reverse order. It was found that enzymatic peptide coupling under the influence of alcalase proceeds cleanly and in high yields, while the resulting dipeptides can be efficiently clicked to acetylene- or azide-containing sugars.
Key words
glycopeptides - azides - alkynes - click chemistry - enzymatic coupling
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