Synthesis of cyclopeptidic analogues of triostin A with quinoxalines or nucleobases as chromophores

被引：30

作者：

Dietrich, B ^{[1
]}

Diederichsen, U ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 01期

关键词：

amino acids; bis(intercalator); cyclic peptides; nucleic acids; triostin A;

D O I：

10.1002/ejoc.200400548

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural antibiotic triostin A (1) is based on a conformationally rigid disulfide-bridged cyclo-octadepsipeptide scaffold. This bicyclic core structure provides a perfect preorganization of two covalently attached quinoxalines resulting in sequence-specific bis(intercalation) of the chromophores in double-stranded DNA. Herein for the first time the corresponding cyclopeptide has been synthesized as a scaffold instead of the cyclodepsipeptide of triostin A by solid-phase peptide synthesis followed by bis(cyclization) in solution. Furthermore, when in contact with DNA the bicyclic peptide provides additional hydrogen-bonding possibilities and greater conformational rigidity in comparison to triostin A. These modifications to the backbone of triostin A might be especially valuable in combination with the use of nucleo-bases instead of quinoxalines for additional DNA recognition next to bis(intercalation) like major groove binding or detection of abasic DNA damages. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

引用

页码：147 / 153

页数：7

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