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A Disulfide Intercalator Toolbox for the Site‐Directed Modification of Polypeptides
Author(s) -
Wang Tao,
Wu Yuzhou,
Kuan Seah Ling,
Dumele Oliver,
Lamla Markus,
Ng David Y. W.,
Arzt Matthias,
Thomas Jessica,
Mueller Jan O.,
BarnerKowollik Christopher,
Weil Tanja
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403965
Subject(s) - bioconjugation , disulfide bond , intercalation (chemistry) , chemistry , surface modification , peptide , combinatorial chemistry , biochemistry , organic chemistry
A disulfide intercalator toolbox was developed for site‐specific attachment of a broad variety of functional groups to proteins or peptides under mild, physiological conditions. The peptide hormone somatostatin (SST) served as model compound for intercalation into the available disulfide functionalization schemes starting from the intercalator or the reactive SST precursor before or after bioconjugation. A tetrazole–SST derivative was obtained that undergoes photoinduced cycloaddition in mammalian cells, which was monitored by live‐cell imaging.