Synthesis of an olefin-containing cyclic peptide using the solid-phase Horner-Emmons reaction

被引：8

作者：

Bang, JK ^{[1
]}

Hasegawa, K ^{[1
]}

Kawakami, T ^{[1
]}

Aimoto, S ^{[1
]}

Akaji, K ^{[1
]}

机构：

[1] Osaka Univ, Inst Prot Res, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 01期

关键词：

olefin peptide; cyclic peptide; solid phase synthesis; Horner-Emmons reaction; HTLV-1; protease;

D O I：

10.1016/j.tetlet.2003.10.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Linear and cyclic olefin peptides containing the substrate sequence for human T-cell leukemia virus type-1 (HTLV-1) were efficiently synthesized on a solid support using the Horner-Emmons reaction. The precursor peptide aldehyde was prepared by oxidation of the corresponding peptide alcohol with Dess-Martin periodinane. The oxidation reaction proceeded quantitatively on a cross-linked ethoxylate acrylate resin (CLEAR) support instead of a polystyrene-based support. Cyclization on the solid support was achieved via an amide bond formation mediated by EDC/HOAt to yield a single major product. The linear olefin peptide was cleaved by HTLV-1 protease at the scissile site, whereas the cyclic olefin peptide functions as a competitive inhibitor rather than a substrate. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：99 / 102

页数：4

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