N ‐Linked Glycosyl Auxiliary‐Mediated Native Chemical Ligation on Aspartic Acid: Application towards  N ‐Glycopeptide Synthesis | Zendy

Chai Hua | Zendy; Le Mai Hoang Kim | Zendy; Vu Minh Duy | Zendy; Pasunooti Kalyan | Zendy; Liu ChuanFa | Zendy; Liu XueWei | Zendy

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N ‐Linked Glycosyl Auxiliary‐Mediated Native Chemical Ligation on Aspartic Acid: Application towards N ‐Glycopeptide Synthesis

Author(s) -

Chai Hua,

Le Mai Hoang Kim,

Vu Minh Duy,

Pasunooti Kalyan,

Liu ChuanFa,

Liu XueWei

Publication year - 2016

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201605597

Subject(s) - glycopeptide , native chemical ligation , glycosyl , chemical ligation , thioester , chemistry , stereochemistry , cleavage (geology) , aspartic acid , oligopeptide , ligation , combinatorial chemistry , chemical synthesis , amino acid , peptide , biochemistry , biology , microbiology and biotechnology , enzyme , paleontology , fracture (geology) , in vitro , antibiotics

A practical approach towards N ‐glycopeptide synthesis using an auxiliary‐mediated dual native chemical ligation (NCL) has been developed. The first NCL connects an N ‐linked glycosyl auxiliary to the thioester side chain of an N‐terminal aspartate oligopeptide. This intermediate undergoes a second NCL with a C‐terminal thioester oligopeptide. Mild cleavage provides the desired N ‐glycopeptide.

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