Efficient synthesis of a side-chain extended diaminodiacid for solid-phase synthesis of peptide disulfide bond mimics

被引：10

作者：

Sun, Shuai-Shuai ^{[1
]}

Chen, Junyou ^{[1
]}

Zhao, Rui ^{[1
]}

Bierer, Donald ^{[3
]}

Wang, Jun ^{[1
]}

Fang, Ge-Min ^{[2
]}

Li, Yi-Ming ^{[1
]}

机构：

[1] Hefei Univ Technol, Anhui Higher Educ Inst, Key Lab Metab & Regulat Major Dis, Sch Food & Biol Engn, Hefei 230009, Anhui, Peoples R China

[2] Anhui Univ, Inst Phys Sci & Informat Technol, Sch Life Sci, Hefei 230601, Anhui, Peoples R China

[3] Bayer AG, Dept Med Chem, Aprather Weg 18A, D-42096 Wuppertal, Germany

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 17期

基金：

中国国家自然科学基金;

关键词：

Disulfide bond mimetic; Diaminodiacid; Five-atom thioether bridge; Oxytocin mimic; CHEMICAL-SYNTHESIS; ANALOGS; DISCOVERY; BRIDGES; PROTEINS;

D O I：

10.1016/j.tetlet.2019.03.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solid-phase incorporation of diaminodiacids is one of the most effective approaches for synthesis of peptide disulfide bond mimics. One of a limitation of current diaminodiacid toolbox is that only four-atom linkage mimics are available that may not fully meet the activity optimization requirement. In this work, we developed a new diaminodiacid that contains a five-atom thioether (C-C-S-C-C) bridge for the first time. With this diaminodiacid in hand, we successfully obtained oxytocin containing new disulfide bond mimic by solid phase peptide synthesis. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：1197 / 1201

页数：5

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