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

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

RSC Adv. 2020 Aug 10;10(49):29373-29377. doi: 10.1039/d0ra06554d. eCollection 2020 Aug 5.

Authors

Hikari Okita¹, Yuna Kato², Tatsuki Masuzawa³, Kosuke Arai², Sayuri Takeo¹, Kohei Sato^{1

2}, Nobuyuki Mase^{1

2

4}, Takanori Oyoshi³, Tetsuo Narumi^{1

2

5}

Affiliations

¹ Department of Applied Chemistry and Biochemical Engineering, Faculty of Engineering, Shizuoka University Shizuoka 432-8561 Japan narumi.tetsuo@shizuoka.ac.jp.
² Department of Engineering, Graduate School of Integrated Science and Technology, Shizuoka University Shizuoka 432-8561 Japan.
³ Department of Chemistry, Graduate School of Integrated Science and Technology, Shizuoka University Shizuoka 422-8529 Japan.
⁴ Green Energy Research Division, Research Institute of Green Science and Technology, Shizuoka University Shizuoka 432-8561 Japan.
⁵ Green Chemistry Research Division, Research Institute of Green Science and Technology, Shizuoka University Shizuoka 432-8561 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.