Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics

Hikari Okita; Yuna Kato; Tatsuki Masuzawa; Kosuke Arai; Sayuri Takeo; Kohei Sato; Nobuyuki Mase; Takanori Oyoshi; Tetsuo Narumi

doi:10.1039/D0RA06554D

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Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics†

Hikari Okita,‡^a Yuna Kato,‡^b Tatsuki Masuzawa,^c Kosuke Arai,^b Sayuri Takeo,^a Kohei Sato,

^ab Nobuyuki Mase,

^abd Takanori Oyoshi^c and Tetsuo Narumi*^abe

Author affiliations

* Corresponding authors

^a Department of Applied Chemistry and Biochemical Engineering, Faculty of Engineering, Shizuoka University, Shizuoka, Japan
E-mail: narumi.tetsuo@shizuoka.ac.jp

^b Department of Engineering, Graduate School of Integrated Science and Technology, Shizuoka University, Shizuoka, Japan

^c Department of Chemistry, Graduate School of Integrated Science and Technology, Shizuoka University, Shizuoka, Japan

^d Green Energy Research Division, Research Institute of Green Science and Technology, Shizuoka University, Shizuoka, Japan

^e Green Chemistry Research Division, Research Institute of Green Science and Technology, Shizuoka University, Shizuoka, Japan

Abstract

Stereoselective and efficient synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres is realized by organocuprate-mediated single electron transfer reduction. The synthetic isosteres can be used in Fmoc-based solid phase peptide synthesis, resulting in the preparation of the 14-mer RGG peptidomimetics containing an (E)-methylalkene or a (Z)-chloroalkene unit.

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Article information

DOI: https://doi.org/10.1039/D0RA06554D
Article type: Paper
Submitted: 06 Jul 2020
Accepted: 30 Jul 2020
First published: 10 Aug 2020
This article is Open Access

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RSC Adv., 2020,10, 29373-29377

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Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics

H. Okita, Y. Kato, T. Masuzawa, K. Arai, S. Takeo, K. Sato, N. Mase, T. Oyoshi and T. Narumi, RSC Adv., 2020, 10, 29373 DOI: 10.1039/D0RA06554D

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Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics†

Abstract

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Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics

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