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Chemoenzymatic Posttranslational Modification Reactions for the Synthesis of Ψ[CH 2 NH]‐Containing Peptides
Author(s) -
Kato Yasuharu,
Kuroda Tomohiro,
Huang Yichao,
Ohta Risa,
Goto Yuki,
Suga Hiroaki
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910894
Subject(s) - isostere , chemistry , peptide , deoxygenation , peptide bond , amide , combinatorial chemistry , chemical synthesis , peptide synthesis , stereochemistry , organic chemistry , catalysis , biochemistry , in vitro
The Ψ[CH 2 NH] reduced amide bond is a peptide isostere widely used in the development of bioactive pseudopeptides. Reported here is a method of chemoenzymatic posttranslational modification for the synthesis of Ψ[CH 2 NH]‐containing peptides converted from ribosomally expressed peptides. The posttranslational conversion composed of an enzymatic cyclodehydration and facile two‐step chemical reduction achieves deoxygenation of a specific amide bond present in a nonprotected peptide in water. This method generates the Ψ[CH 2 NH] bond in peptides and is applicable to various peptide sequences, potentially enabling the preparation of a library of Ψ[CH 2 NH]‐containing peptides.