Traceless synthesis of protein thioesters using enzyme-mediated hydrazinolysis and subsequent self-editing of the cysteinyl prolyl sequence

Chiaki Komiya; Akira Shigenaga; Jun Tsukimoto; Masahiro Ueda; Takuya Morisaki; Tsubasa Inokuma; Kohji Itoh; Akira Otaka

doi:10.1039/C9CC03583D

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Traceless synthesis of protein thioesters using enzyme-mediated hydrazinolysis and subsequent self-editing of the cysteinyl prolyl sequence†

Chiaki Komiya,

^a Akira Shigenaga,

*^a Jun Tsukimoto,

^b Masahiro Ueda,

^a Takuya Morisaki,^a Tsubasa Inokuma,

^a Kohji Itoh^b and Akira Otaka

*^a

Author affiliations

* Corresponding authors

^a Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan
E-mail: aotaka@tokushima-u.ac.jp, shigenaga.akira@tokushima-u.ac.jp

^b Institute of Medicinal Resources, Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan

Abstract

A traceless thioester-producing protocol featuring carboxypeptidase Y-mediated hydrazinolysis of cysteinyl prolyl leucine-tagged peptides has been developed. The hydrazinolysis followed by thioesterification affords cysteinyl prolyl thioesters. Self-editing of the tag and subsequent trans-thioesterification yields peptide thioesters. The developed protocol was successfully applied to the conversion of recombinant proteins to thioesters.

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Article information

DOI: https://doi.org/10.1039/C9CC03583D
Article type: Communication
Submitted: 09 May 2019
Accepted: 23 May 2019
First published: 23 May 2019

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Chem. Commun., 2019,55, 7029-7032

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Traceless synthesis of protein thioesters using enzyme-mediated hydrazinolysis and subsequent self-editing of the cysteinyl prolyl sequence

C. Komiya, A. Shigenaga, J. Tsukimoto, M. Ueda, T. Morisaki, T. Inokuma, K. Itoh and A. Otaka, Chem. Commun., 2019, 55, 7029 DOI: 10.1039/C9CC03583D

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Chemical Communications

Traceless synthesis of protein thioesters using enzyme-mediated hydrazinolysis and subsequent self-editing of the cysteinyl prolyl sequence†

Abstract

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Traceless synthesis of protein thioesters using enzyme-mediated hydrazinolysis and subsequent self-editing of the cysteinyl prolyl sequence

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