The New Metabolite (S)-Cinnamoylphosphoramide from Streptomyces sp and Its Total Synthesis

被引：8

作者：

Quitschau, Melanie ^{[1
]}

Schuhmann, Tim ^{[1
]}

Piel, Joern ^{[2
]}

von Zezschwitz, Paultheo ^{[1
]}

Grond, Stephanie ^{[1
]}

机构：

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

[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 30期

关键词：

Configuration determination; Natural products; Phosphorus; Streptomyces; Total synthesis;

D O I：

10.1002/ejoc.200800654

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tunicate-associated strain Streptomyces sp. JP90 produces the unprecedented metabolite cinnamoylphosphoramide (1) among several other compounds. Structure elucidation was accomplished by NMR spectroscopic studies and efficient total synthesis. The absolute configuration at phosphorus was determined by synthesis of both enantiomers of 1 performing a resolution of the corresponding diastereomeric phosphoramides of L-phenylalanine ethyl ester. Unusual cinnamic acid derivative 1 represents the first bacterial organophosphoramide. As it matches the Schrader's formula for insecticidal organophosphates, its biological activity was investigated. A weak inhibition of acetylcholinesterase was observed in in vitro tests, and water-soluble analogues of 1 were prepared. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

引用

页码：5117 / 5124

页数：8

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