Chemistry of glycopeptides

Kunz, Horst; Löhr, Birgit; Habermann, J.

doi:10.1007/978-94-015-9281-9_5

Carbohydrates 1999

DOI: 10.1007/978-94-015-9281-9_5

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Chemistry of glycopeptides

Horst Kunz

Birgit Löhr

J. Habermann

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Cited by 2 publications

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Efficient Synthesis of S‐Linked Glycopeptides in Aqueous Solution by a Convergent Strategy

Zhu

Schmidt

2004

Chemistry A European J

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In naturally occurring glycopeptides and glycoproteins the glycan residues generally possess N- and O-linkages to the peptide backbone. Here we report the synthesis of the corresponding S-linked glycopeptides by a convergent strategy to provide compounds which should be quite stable to glycosidases. To this end, peptides that contain beta-bromoalanine and gamma-bromohomoalanine were generated either directly by bromination of serine and homoserine residues, respectively, or by standard ligation of the corresponding amino acids. 1-Thiosugars of O-acetyl protected GalNAc, GlcNAc, and lactose were prepared by known procedures. Reaction of the thiosugars with these peptides in an ethyl acetate/water two-phase system, which contained TBAHS and NaHCO(3), or in a one-phase system that consists of DMF/water and which contains NaHCO(3), led to the desired S-linked glycopeptides cleanly and in almost quantitative yield. This reaction also worked well for O-unprotected 1-thiosugars.

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Efficient Synthesis of S‐Linked Glycopeptides in Aqueous Solution by a Convergent Strategy

Zhu

Schmidt

2004

Chemistry A European J

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ChemInform Abstract: Chemistry of Glycopeptides

2000

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Chemistry of glycopeptides

Cited by 2 publications

References 132 publications

Efficient Synthesis of S‐Linked Glycopeptides in Aqueous Solution by a Convergent Strategy

Efficient Synthesis of S‐Linked Glycopeptides in Aqueous Solution by a Convergent Strategy

ChemInform Abstract: Chemistry of Glycopeptides

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