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Native N-glycopeptide thioester synthesis through N?S acyl transfer.

ABSTRACT: Peptide thioesters are important tools for the total synthesis of proteins using native chemical ligation (NCL). Preparation of glycopeptide thioesters, that enable the assembly of homogeneously glycosylated proteins, is complicated by the perceived fragile nature of the sugar moiety. Herein, we demonstrate the compatibility of thioester formation via N?S acyl transfer with native N-glycopeptides and report observations that will aid in their preparation.

SUBMITTER: Premdjee B

PROVIDER: S-EPMC3160546 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Native N-glycopeptide thioester synthesis through N→S acyl transfer.

Premdjee Bhavesh B Adams Anna L AL Macmillan Derek D

Bioorganic & medicinal chemistry letters 20110525 17

Peptide thioesters are important tools for the total synthesis of proteins using native chemical ligation (NCL). Preparation of glycopeptide thioesters, that enable the assembly of homogeneously glycosylated proteins, is complicated by the perceived fragile nature of the sugar moiety. Herein, we demonstrate the compatibility of thioester formation via N→S acyl transfer with native N-glycopeptides and report observations that will aid in their preparation. ...[more]

PMID: 21676613

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