On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation

被引：10

作者：

Serra, Gloria ^{[1
]}

Posada, Laura ^{[1
]}

Hojo, Hironobu ^{[2
]}

机构：

[1] Univ Republica, Fac Quim, Dept Quim Organ, Quim Farmaceut, Gen Flores 2124,CC 1157, Montevideo, Uruguay

[2] Osaka Univ, Inst Prot Res, Suita, Osaka 5650871, Japan

来源：

CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 06期

关键词：

CYSTEINE; MACROCYCLES; DESULFURIZATION;

D O I：

10.1039/c9cc07783a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

On-resin intramolecular native chemical ligation (NCL) assisted by N-ethylcysteine using Fmoc/SPPS to obtain cyclic peptides is described. N-terminal cysteine-containing peptides were subjected to NCL conditions leading to cyclization-cleavage reactions and consecutive S -> N shift, rendering cyclic peptides in good yields and purities. The compounds were evaluated against P. falciparum 3D7.

引用

页码：956 / 959

页数：4

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