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Biosynthesis of Carbapenem Antibiotics: New Carbapenam Substrates for Carbapenem Synthase (CarC)
Author(s) -
Sleeman Mark C.,
Smith Paul,
Kellam Barrie,
Chhabra Siri Ram,
Bycroft Barrie W.,
Schofield Christopher J.
Publication year - 2004
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.200300908
Subject(s) - carbapenem , biosynthesis , oxygenase , stereochemistry , chemistry , substrate (aquarium) , atp synthase , thienamycin , antibiotics , combinatorial chemistry , biochemistry , biology , enzyme , ecology
A non‐haem iron and 2‐oxoglutarate oxygenase, CarC catalyses the highly unusual epimerisation and desaturation of a (3 S ,5 S )‐carbapenam 2 to give a (5 R )‐carbapenem 1 . All stereoisomers of 2 were synthesised and analysed as CarC substrates. The results imply that the (3 S ,5 R )‐carbapenam is an intermediate in carbapenem biosynthesis and that CarC is able to accept unnatural stereoisomers of its carbapenam substrate.