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Issue 49, 2020
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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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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.

Graphical abstract: 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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Article information


Submitted
06 Jul 2020
Accepted
30 Jul 2020
First published
10 Aug 2020

This article is Open Access

RSC Adv., 2020,10, 29373-29377
Article type
Paper

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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