Facile solid-phase synthesis of cyclic decapeptide antibiotic streptocidins A–D

First total synthesis of streptocidins A–D is reported. Total synthesis of decapeptide antibiotics streptocidins A–D from Streptomyces sp. Tü 6071 was accomplished for the first time by solid-phase peptide synthesis followed by traceless cyclization of the activated linear precursors, without protec...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 1; pp. 217 - 220
Main Authors Qin, Chuanguang, Zhong, Xiaofen, Ng, Na Lee, Bu, Xianzhang, Chan, Wing Sze, Guo, Zhihong
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
LIBRARIES
SAFETY-CATCH LINKER
SIMILAR-TO-D
PEPTIDES
HEMOLYTIC ACTIVITIES
ANALOGS
GRAMICIDIN-S
CYCLIZATION
THIOESTERASE DOMAIN
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Summary:First total synthesis of streptocidins A–D is reported. Total synthesis of decapeptide antibiotics streptocidins A–D from Streptomyces sp. Tü 6071 was accomplished for the first time by solid-phase peptide synthesis followed by traceless cyclization of the activated linear precursors, without protection of nucleophilic side chain. Synthetic products were equally active as the natural products isolated from the bacterial source and found to possess similar bacterial selectivity as other members in the amphipathic antimicrobial cyclic decapeptide family.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.10.134