Expedient Synthesis of Triazole-Linked Glycosyl Amino Acids and Peptides

An expedient, high-yielding synthesis of two types of triazole-linked glycopeptides is described. These novel and stable glycopeptide mimics were prepared via Cu(I)-catalyzed [3 + 2] cycloaddition of either azide-functionalized glycosides and acetylenic amino acids or acetylenic glycosides and azide...

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Bibliographic Details
Published in:Organic letters 2004-09, Vol.6 (18), p.3123-3126
Main Authors: Kuijpers, Brian H. M, Groothuys, Stan, Keereweer, A. (Bram) R, Quaedflieg, Peter J. L. M, Blaauw, Richard H, van Delft, Floris L, Rutjes, Floris P. J. T
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Catalysis
Copper - chemistry
Glycopeptides - analysis
Glycopeptides - chemical synthesis
Glycopeptides - chemistry
Glycosides - chemical synthesis
Glycosides - chemistry
Indicators and Reagents
Molecular Structure
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:An expedient, high-yielding synthesis of two types of triazole-linked glycopeptides is described. These novel and stable glycopeptide mimics were prepared via Cu(I)-catalyzed [3 + 2] cycloaddition of either azide-functionalized glycosides and acetylenic amino acids or acetylenic glycosides and azide-containing amino acids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048841o