Solid-phase synthesis of cyclic hexapeptides wollamides A, B and desotamide B

被引：15

作者：

Tsutsumi, Lissa S. ^{[1
]}

Tan, Ghee T. ^{[1
]}

Sun, Dianqing ^{[1
]}

机构：

[1] Univ Hawaii, Daniel K Inouye Coll Pharm, Dept Pharmaceut Sci, 34 Rainbow Dr, Hilo, HI 96720 USA

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 27期

关键词：

Cyclohexapeptide; Desotamide B; Macrocyclization; Macrolactamization; Solid-phase synthesis; Wollamide A; Wollamide B; MACROCYCLIZATION; STREPTOMYCES; PEPTIDES; REAGENTS;

D O I：

10.1016/j.tetlet.2017.05.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solid-phase synthesis of antibacterial cyclohexapeptides including wollamides A, B and desotamide B has been developed. Briefly, the protected linear hexapeptides were assembled on 2-chlorotrityl chloride resin using standard Fmoc chemistry and diisopropylcarbodiimide/hydroxybenzotriazole coupling reagents, cleaved off-resin with hexafluoroisopropanol/dichloromethane to keep side-chain protecting groups intact, and cyclized in solution. Final global removal of all protecting groups using a cocktail of trifluoroacetic acid/triisopropylsilane/dichloromethane afforded the desired cyclic hexapeptides, which were characterized by H-1,C-13 NMR, and HRMS. Subsequent investigation of macrocyclization parameters such as terminal residues, coupling reagents, and cyclization concentration revealed the optimized conditions for the synthesis of this class of cyclic hexapeptides. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2675 / 2680

页数：6

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