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Synthesis of hemithioindigo‐based chromopeptides by using the Tmb auxiliary in native chemical ligation studies
Author(s) -
Kitzig S.,
RückBraun K.
Publication year - 2017
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.3001
Subject(s) - tcep , native chemical ligation , thioester , chemistry , phosphine , adduct , tris , yield (engineering) , cleavage (geology) , peptide , amino acid , stereochemistry , biochemistry , combinatorial chemistry , chemical synthesis , organic chemistry , in vitro , enzyme , biology , catalysis , paleontology , materials science , fracture (geology) , metallurgy
The 4,5,6‐trimethoxy‐2‐mercaptobenzyl auxiliary was used in auxiliary‐based native chemical ligation reactions with Boc‐protected p HTI and m HTI ω ‐amino acid thioesters 2a , b for the construction of small hemithioindigo (HTI)‐based chromopeptides 6a , b with a class 1 PDZ binding motif. While reversible tris(2‐carboxyethyl)phosphine (TCEP)‐HTI adduct formation required moderate use of access TCEP, the Na ascorbate concentration was broadly varied for optimization of the reaction conditions. In the studies presented, the m HTI ω ‐amino acid thioester 2b proved to be slightly less reactive than the p HTI ω ‐amino acid thioester 2a . Ligated products 5a – d were isolated in 35–81% yield, and also cleavage of the auxiliary proceeded smoothly, furnishing peptides 6a – d in 48–61% yield. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.