Head-to-tail macrocyclization of cysteine-free peptides using an o-aminoanilide linker

被引：16

作者：

Ohara, Takumi ^{[1
]}

Kaneda, Masato ^{[1
]}

Saito, Tomo ^{[1
]}

Fujii, Nobutaka ^{[1
]}

Ohno, Hiroaki ^{[1
]}

Oishi, Shinya ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2018年 / 28卷 / 08期

关键词：

Chemokine; CXCR4; antagonist; Cyclic peptide; Macrocyclization; Microflow reaction; SOLID-PHASE-SYNTHESIS; SAFETY-CATCH LINKER; NATIVE CHEMICAL LIGATION; NEXT-GENERATION THERAPEUTICS; AMIDE BOND FORMATION; CYCLIC-PEPTIDES; CXCR4; ANTAGONISTS; OXIME RESIN; CYCLIZATION; PROTEINS;

D O I：

10.1016/j.bmcl.2018.03.027

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A head-to-tail macrocyclization protocol for the preparation of cysteine- free cyclic peptides was investigated. The o-aminoanilide linker constructed in the peptide sequence by a standard Fmoc-based peptide synthesis procedure was subjected to nitrite-mediated activation under acidic conditions toward N-acyl benzotriazole as the active ester species. The subsequent cyclization smoothly proceeded by neutralization in the presence of additives such as 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) to afford the expected cyclic pentapeptide, a CXCR4 antagonist. The cyclization efficiencies were dependent on the precursor open-chain sequence. The application of this step-wise activation-cyclization protocol to microflow reaction systems is also described. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1283 / 1286

页数：4

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