Synthesis of 1,2,3-Triazole-Linked Glycoconjugates of N-(2-Aminoethyl)glycine: Building Blocks for the Construction of Combinatorial Glycopeptide Libraries

Kai Uwe Günther; Thomas Ziegler

doi:10.1055/s-0033-1339137

Synthesis, Table of Contents

Synthesis 2014; 46(17): 2362-2370
DOI: 10.1055/s-0033-1339137

paper

Synthesis of 1,2,3-Triazole-Linked Glycoconjugates of N-(2-Aminoethyl)glycine: Building Blocks for the Construction of Combinatorial Glycopeptide Libraries

Authors

Kai Uwe Günther

Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany Fax: +49(7071)295244 Email: thomas.ziegler@uni-tuebingen.de
Thomas Ziegler*

Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany Fax: +49(7071)295244 Email: thomas.ziegler@uni-tuebingen.de

Abstract

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Abstract

Twenty-nine glycoconjugate building blocks based on the N-(2-aminoethyl)glycine (AEG) backbone and sugars linked to the backbone by a 1,2,3-triazole moiety were prepared via copper-catalyzed 1,3-dipolar cycloaddition of monosaccharides bearing an azide group and N-4-pentynoyl-AEG. The initial glycoconjugates were converted to the corresponding acids and pentafluorophenyl esters, respectively, which are useful building blocks for the construction of combinatorial glycopeptide libraries.

Key words

carbohydrates - glycopeptides - glycoconjugates - amino acids - azides

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References

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Supplementary Material

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