Organic Chemistry

Fmoc-Compatible and External-Thiol-Free Peptide C-Terminus Alkyl Thioester Formation Using Cysteinylprolyl Imide

Akimitsu Okamoto The University of Tokyo

Abstract

We report an Fmoc-compatible and external-thiol-free method of peptide C-terminus thioesterification with cysteinylprolyl imide. The newly synthesized structure, i.e., cysteinylprolyl-thiazolidinone, provided high conversion and sequence-independent fast kinetics (90 min) in the diketopiperazine thioester formation under relatively mild conditions: pH 6.0, 37 °C. Employing this thioesterification method, we synthesized histone H3.2 bearing K56 acetylation.

Content

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Supplementary material

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SI Fmoc-compatible and External-thiol-free Peptide C-terminus Alkyl-thioester Formation Using Cysteinylprolyl Imide (CPI) okamoto2