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Ribosomal Synthesis of Cyclic Peptides with a Fluorogenic Oxidative Coupling Reaction
Author(s) -
Yamagishi Yusuke,
Ashigai Hiroshi,
Goto Yuki,
Murakami Hiroshi,
Suga Hiroaki
Publication year - 2009
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200900021
Subject(s) - oxidative coupling of methane , chemistry , conjugated system , oxidative phosphorylation , combinatorial chemistry , stereochemistry , fluorescence , amino acid , benzylamine , biochemistry , organic chemistry , catalysis , physics , quantum mechanics , polymer
Ring around the peptides : We demonstrate a new method for the cyclization of peptides that involves the oxidative coupling of 5‐hydroxyindole and benzylamine. After two nonproteinogenic amino acids were incorporated into peptides by reprogramming the genetic code, cyclization took place rapidly upon the addition of K 3 Fe(CN) 6 and generated a conjugated, fluorescent, heterocyclic structure.