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Evidence that Thienamycin Biosynthesis Proceeds via C‐5 Epimerization: ThnE Catalyzes the Formation of (2 S ,5 S )‐ trans ‐Carboxymethylproline
Author(s) -
Hamed Refaat B.,
Batchelar Edward T.,
Mecinović Jasmin,
Claridge Timothy D. W.,
Schofield Christopher J.
Publication year - 2009
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200800652
Subject(s) - thienamycin , biosynthesis , epimer , stereochemistry , aldehyde , chemistry , enzyme , biochemistry , antibiotics , catalysis
Unusual antibiotic biosynthesis enzymes : The observation that formation of trans ‐carboxymethylproline ( t ‐CMP) and 6‐methyl‐ t ‐CMP is catalyzed by ThnE from Streptomyces cattleya using glutamate semi‐aldehyde and malonyl‐ or methylmalonyl‐CoA implies the need for a C‐5 epimerization step in the biosynthesis of thienamycin and reveals the possibility that a methyl group at C‐6 might be introduced at an early stage.