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甘氨酰-甘氨酸型()-甲基烯烃和()-氯烯烃二肽类似物的立体选择性合成及其在14聚体RGG拟肽中的应用。

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

作者信息

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

机构信息

Department of Applied Chemistry and Biochemical Engineering, Faculty of Engineering, Shizuoka University Shizuoka 432-8561 Japan

Department of Engineering, Graduate School of Integrated Science and Technology, Shizuoka University Shizuoka 432-8561 Japan.

出版信息

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

Abstract

Stereoselective and efficient synthesis of Gly-Gly-type ()-methylalkene and ()-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 ()-methylalkene or a ()-chloroalkene unit.

摘要

通过有机铜酸盐介导的单电子转移还原反应,实现了甘氨酰-甘氨酸型()-甲基烯烃和()-氯烯烃二肽类似物的立体选择性高效合成。合成的类似物可用于基于Fmoc的固相肽合成,从而制备出含有()-甲基烯烃或()-氯烯烃单元的14聚体RGG肽模拟物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/868c/9055925/b5d5479fc18a/d0ra06554d-f1.jpg

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