154333-41-2Relevant academic research and scientific papers
Enzyme-catalysed synthesis and absolute configuration assignments of cis-dihydrodiol metabolites from 1,4-disubstituted benzenes
Boyd, Derek R.,Sharma, Narain D.,Coen, Gerard P.,Gray, Peter J.,Malone, John F.,Gawronski, Jacek
, p. 5804 - 5811 (2008/02/13)
A series of ten cis-dihydrodiol metabolites has been obtained by bacterial biotransformation of the corresponding 1,4-disubstituted benzene substrates using Pseudomonas putida UV4, a source of toluene dioxygenase (TDO). Their enantiomeric excess (ee) values have been established using chiral stationary phase HPLC and 1H NMR spectroscopy. Absolute con_figurations of the majority of cis-dihydrodiols have been established using stereochemical correlation and X-ray crystallography and the remainder have been tentatively assigned using NMR spectroscopic methods but finally confirmed by circular dichroism (CD) spectroscopy. These configurational assignments support and extend the validity of an empirical model, previously used to predict the preferred stereochemistry of TDO-catalysed cis-dihydroxylation of ten 1,4-disubstituted benzene substrates, to more than twenty-five examples.
Chemoenzymatic synthesis of the trans-dihydrodiol isomers of monosubstituted benzenes via anti-benzene dioxides
Boyd, Derek R.,Sharma, Narain D.,Llamas, Nuria M.,O'Dowd, Colin R.,Allen, Christopher C. R.
, p. 2208 - 2217 (2008/02/09)
Enantiopure cis-2,3-dihydrodiols, available from dioxygenase-catalysed cis-dihydroxylation of monosubstituted benzene substrates, have been used as synthetic precursors of the corresponding trans-3,4-dihydrodiols. The six-step chemoenzymatic route from ci
Enantioselective Bacterial Biotransformation Routes to cis-Diol Metabolites of Monosubstituted Benzenes, Naphthalene and Benzocycloalkenes of Either Absolute Configuration
Allen, Christopher C. R.,Boyd, Derek R.,Dalton, Howard,Sharma, Narain D.,Brannigan, Ian,et al.
, p. 117 - 118 (2007/10/02)
Enzyme-catalysed kinetic resolution and asymmetric dihydroxylation routes to enantiopure cis-diol metabolites of arenes and benzocycloalkenes of either absolute configuration have been developed using appropriate strains of the bacterium Pseudomonas putida.
