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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.