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

共 4 条

[1] Synthesis of selenocysteine-containing cyclic peptides via tandem N-to-S acyl migration and intramolecular selenocysteine-mediated native chemical ligation
Shimodaira, Shingo
Takei, Toshiki
Hojo, Hironobu
Iwaoka, Michio
CHEMICAL COMMUNICATIONS, 2018, 54 (83) : 11737 - 11740
[2] Acceleration of thiol additive-free native chemical ligation by intramolecular S → S acyl transfer
Schmalisch, J.
Seitz, O.
CHEMICAL COMMUNICATIONS, 2015, 51 (35) : 7554 - 7557
[3] Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters
Terrier, Victor P.
Delmas, Agnes F.
Aucagne, Vincent
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (02) : 316 - 319
[4] Long-Range Intramolecular S → N Acyl Migration: A Study of the Formation of Native Peptide Analogues via 13-, 15-, and 16-Membered Cyclic Transition States
Ha, Khanh
Chahar, Mamta
Monbaliu, Jean-Christophe M.
Todadze, Ekaterina
Hansen, Finn K.
Oliferenko, Alexander A.
Ocampo, Charles E.
Leino, David
Lillicotch, Aaron
Stevens, Christian V.
Katritzky, Alan R.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06): : 2637 - 2648

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