Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

Klaus Villadsen; Manuel Cristo Martos Maldonado; Knud Jørgen Jensen; Mikkel Boas Thygesen

doi:10.1002/cbic.201600582

Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

Klaus Villadsen, Manuel Cristo Martos Maldonado, Knud Jørgen Jensen^*, Mikkel Boas Thygesen

^*Corresponding author for this work

Department of Chemistry

42 Citations (Scopus)

Abstract

Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its “omics”, glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.

Original language	English
Journal	ChemBioChem
Volume	18
Issue number	7
Pages (from-to)	574-612
Number of pages	39
ISSN	1439-4227
DOIs	https://doi.org/10.1002/cbic.201600582
Publication status	Published - 2017

Keywords

carbohydrate–protein interactions
glycan tagging
glycobiology
glycoconjugates
glycoproteins

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10.1002/cbic.201600582

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abstract = "Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its “omics”, glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.",

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AU - Villadsen, Klaus

AU - Martos Maldonado, Manuel Cristo

AU - Jensen, Knud Jørgen

AU - Thygesen, Mikkel Boas

PY - 2017

Y1 - 2017

N2 - Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its “omics”, glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.

AB - Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its “omics”, glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.

KW - carbohydrate–protein interactions

KW - glycan tagging

KW - glycobiology

KW - glycoconjugates

KW - glycoproteins

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DO - 10.1002/cbic.201600582

M3 - Review

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AN - SCOPUS:85014036661

SN - 1439-4227

VL - 18

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JO - ChemBioChem

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Chemoselective Reactions for the Synthesis of Glycoconjugates from Unprotected Carbohydrates

Abstract

Keywords

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