title: Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols.
abstract: Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations.
authors.affiliation: School of Chemistry and Chemical Engineering, Queen's University, Belfast, BT9 5AG, UK. dr.boyd@qub.ac.uk
authors.forename: Derek R
authors.initials: DR
authors.lastname: Boyd
authors.forename: Narain D
authors.initials: ND
authors.lastname: Sharma
authors.forename: John F
authors.initials: JF
authors.lastname: Malone
authors.forename: Peter B A
authors.initials: PB
authors.lastname: McIntyre
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Stevenson
authors.forename: Christopher C R
authors.initials: CC
authors.lastname: Allen
authors.forename: Marcin
authors.initials: M
authors.lastname: Kwit
authors.forename: Jacek
authors.initials: J
authors.lastname: Gawronski
mesh_terms: D055162:Biocatalysis; D001711:Biotransformation; D020134:Catalytic Domain; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D053138:Cyclohexenes / Q000737:chemistry*; D006018:Glycols / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D010105:Oxygenases / Q000737:chemistry / Q000378:metabolism; D019800:Phenol / Q000378:metabolism*; D016958:Pseudomonas putida / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D053138:Cyclohexenes; D006018:Glycols; C052568:cyclohexene; D019800:Phenol; D010105:Oxygenases; C023172:toluene dioxygenase