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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)