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Development of Efficient Methods for Accomplishing Cysteine‐Free Peptide and Glycopeptide Coupling
Author(s) -
Chen Gong,
Wan Qian,
Tan Zhongping,
Kan Cindy,
Hua Zihao,
Ranganathan Krishnakumar,
Danishefsky Samuel J.
Publication year - 2007
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.200702865
Subject(s) - tcep , thioester , peptide , chemistry , cysteine , glycopeptide , alkyl , moiety , tris , combinatorial chemistry , stereochemistry , phosphine , biochemistry , organic chemistry , antibiotics , enzyme , catalysis
As simple as A, B, C : Non‐cysteine‐based reiterative fragment coupling of glycopeptides involves a metal‐free (TCEP) coupling of a peptidyl C‐terminal phenolic ester containing an ortho ‐disulfide moiety (A) with an N‐terminal glycopeptide whose C terminus is an alkyl thioester (B) to produce AB, whose N terminus contains an alkyl thioester. A AgCl‐mediated coupling of AB with peptide C then produces the tridomainal peptide ABC. TCEP=tris(2‐carboxyethyl)phosphine.
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