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

preprint
submitted on 29.04.2020 and posted on 29.04.2020 by Koki Nakatsu, Masafumi Yanase, Gosuke Hayashi, Akimitsu Okamoto
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.

History

Email Address of Submitting Author

okamoto@chembio.t.u-tokyo.ac.jp

Institution

The University of Tokyo

Country

Japan

ORCID For Submitting Author

0000-0002-7418-6237

Declaration of Conflict of Interest

None

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