Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters

被引：23

作者：

Terrier, Victor P. ^{[1
]}

Delmas, Agnes F. ^{[1
]}

Aucagne, Vincent ^{[1
]}

机构：

[1] CNRS UPR 4301, Ctr Biophys Mol, Rue Charles Sadron, F-45071 Orleans 2, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 02期

关键词：

ACYL TRANSFER; PROTEINS; STRATEGY; CYCLIZATION; CYCLOTIDES; INHIBITORS; DEFENSINS; CHEMISTRY; DISCOVERY; ORIGIN;

D O I：

10.1039/c6ob02546c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein introduce a straightforward synthetic route to cysteine-containing cyclic peptides based on the intramolecular native chemical ligation of in situ generated thioesters. Key precursors are N-Hnb-Cys crypto-thioesters, easily synthesized by Fmoc-based SPPS. The strategy is applied to a representative range of naturally occurring cyclic disulfide-rich peptide sequences.

引用

页码：316 / 319

页数：4

共 5 条

[1] N-2-hydroxybenzyl-cysteine peptide crypto-thioesters for native chemical ligation
Amoura, Mehdi
Sarraf, Daad
Nauton, Lionel
Terrier, Victor
Lelievre, Dominique
Gautier, Arnaud
Servent, Denis
Kessler, Pascal
Delmas, Agnes
Aucagne, Vincent
JOURNAL OF PEPTIDE SCIENCE, 2018, 24 : S56 - S57
[2] Second generation N-2-hydroxybenzyl-cysteine peptide crypto-thioesters for native chemical ligation
Amoura, Mehdi
Terrier, Victor
Delmas, Agnes
Aucagne, Vincent
JOURNAL OF PEPTIDE SCIENCE, 2018, 24 : S100 - S101
[3] Synthesis of Cysteine-Rich Peptides by Native Chemical Ligation without Use of Exogenous Thiols
Tsuda, Shugo
Yoshiya, Taku
Mochizuki, Masayoshi
Nishiuchi, Yuji
ORGANIC LETTERS, 2015, 17 (07) : 1806 - 1809
[4] On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation
Serra, Gloria
Posada, Laura
Hojo, Hironobu
CHEMICAL COMMUNICATIONS, 2020, 56 (06) : 956 - 959
[5] 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

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