The New Metabolite ( S )‐Cinnamoylphosphoramide from  Streptomyces  sp. and Its Total Synthesis | Zendy

Quitschau Melanie | Zendy; Schuhmann Tim | Zendy; Piel Jörn | Zendy; von Zezschwitz Paultheo | Zendy; Grond Stephanie | Zendy

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

Author(s) -

Quitschau Melanie,

Schuhmann Tim,

Piel Jörn,

von Zezschwitz Paultheo,

Grond Stephanie

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800654

Subject(s) - chemistry , stereochemistry , diastereomer , total synthesis , metabolite , absolute configuration , enantiomer , streptomyces , derivative (finance) , organic chemistry , biochemistry , bacteria , biology , financial economics , economics , genetics

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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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