Development of Novel Amino Acids Containing N-mercaptophenetyl (MPE)-type Auxiliary and Orthogonal Protecting Groups for Sequential Ligation of Multiple Peptides

被引：0

作者：

Taguchi, Yoshinori ^{[1
]}

Watanabe, Kohei ^{[2
]}

Sato, Kohei ^{[2
]}

Mase, Nobuyuki ^{[2
]}

Narumi, Tetsuo ^{[1
,2
]}

机构：

[1] Shizuoka Univ, Grad Sch Med Photon, Hamamatsu, Shizuoka 4328561, Japan

[2] Shizuoka Univ, Grad Sch Integrated Sci & Technol, Hamamatsu, Shizuoka 4328561, Japan

来源：

CHEMISTRYSELECT | 2024年 / 9卷 / 27期

关键词：

Chemical protein synthesis; Ligation auxiliaries; Orthogonal protection; Sequential peptide ligation; NATIVE CHEMICAL LIGATION; PROTEIN-SYNTHESIS; GLYCINE;

D O I：

10.1002/slct.202402339

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemoselective peptide ligation using ligation auxiliaries is a powerful methodology to extend the scope of native chemical ligation beyond ligation at Cys. Herein, we report the development of novel amino acids containing an N-mercaptophenethyl (MPE)-type auxiliary and protecting groups (i. e., tert-butyloxycarbonyl (Boc), 1,3-thiazolidine (Thz), and allyloxycarbonyl (Alloc)). These developed amino acids can be introduced into a peptide via 9-fluorenylmethoxycarbonyl-based solid-phase peptide synthesis, enabling deprotection and native chemical ligation in one pot. The combination of Thz-type and Alloc-type acids enables sequential peptide ligation, which is applicable to the synthesis of peptides branched from a Lys side chain. We also found that the multiple N-MPE groups are efficiently cleaved upon treatment with tris(2-carboxyethyl)phosphine and morpholine in the presence of SnCl2.

引用

页数：4