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

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...

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Autores principales: Okita, Hikari, Kato, Yuna, Masuzawa, Tatsuki, Arai, Kosuke, Takeo, Sayuri, Sato, Kohei, Mase, Nobuyuki, Oyoshi, Takanori, Narumi, Tetsuo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055925/
https://www.ncbi.nlm.nih.gov/pubmed/35521116
http://dx.doi.org/10.1039/d0ra06554d
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author Okita, Hikari
Kato, Yuna
Masuzawa, Tatsuki
Arai, Kosuke
Takeo, Sayuri
Sato, Kohei
Mase, Nobuyuki
Oyoshi, Takanori
Narumi, Tetsuo
author_facet Okita, Hikari
Kato, Yuna
Masuzawa, Tatsuki
Arai, Kosuke
Takeo, Sayuri
Sato, Kohei
Mase, Nobuyuki
Oyoshi, Takanori
Narumi, Tetsuo
author_sort Okita, Hikari
collection PubMed
description 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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spelling pubmed-90559252022-05-04 Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics Okita, Hikari Kato, Yuna Masuzawa, Tatsuki Arai, Kosuke Takeo, Sayuri Sato, Kohei Mase, Nobuyuki Oyoshi, Takanori Narumi, Tetsuo RSC Adv Chemistry 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. The Royal Society of Chemistry 2020-08-10 /pmc/articles/PMC9055925/ /pubmed/35521116 http://dx.doi.org/10.1039/d0ra06554d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Okita, Hikari
Kato, Yuna
Masuzawa, Tatsuki
Arai, Kosuke
Takeo, Sayuri
Sato, Kohei
Mase, Nobuyuki
Oyoshi, Takanori
Narumi, Tetsuo
Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics
title Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics
title_full Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics
title_fullStr Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics
title_full_unstemmed Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics
title_short Stereoselective synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres and their application to 14-mer RGG peptidomimetics
title_sort stereoselective synthesis of gly-gly-type (e)-methylalkene and (z)-chloroalkene dipeptide isosteres and their application to 14-mer rgg peptidomimetics
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055925/
https://www.ncbi.nlm.nih.gov/pubmed/35521116
http://dx.doi.org/10.1039/d0ra06554d
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