Peptidyl N-alkylcysteine as a peptide thioester surrogate in the native chemical ligation

被引：28
作者：
Asahina, Yuya [1 ]
Nabeshima, Kei [2 ]
Hojo, Hironobu [1 ]
机构：
[1] Osaka Univ, Inst Prot Res, Suita, Osaka 5650871, Japan
[2] Tokyo Metropolitan Univ, Grad Sch Sci & Engn, Tokyo 1920397, Japan
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 11期
关键词：
Peptide thioester; Thioesterification; N-to-S acyl device; N-Alkylcysteine (NAC); Native chemical ligation (NCL); CHEMOENZYMATIC SYNTHESIS; POLYPEPTIDE-SYNTHESIS; PROTEIN; SEGMENT; DOMAIN;
D O I：
10.1016/j.tetlet.2015.01.095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Peptides having the C-terminal N-alkylcysteine (NAC) with a free carboxy group, which can be easily prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS), was directly used for the native chemical ligation (NCL) based on the in situ thioesterification method. The reaction efficiently proceeded under a mild acidic condition (pH similar to 5) to give the ligated product. This method was successfully used for the synthesis of the human brain natriuretic peptide, (BNP)-32, showing the usefulness of the peptidyl NAC as a thioester surrogate for the NCL reaction. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1370 / 1373
页数：4
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