828295-31-4Relevant academic research and scientific papers
Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates
Boyd, Derek R.,Sharma, Narain D.,Ljubez, Vera,McGeehin, Peter K. M.,Stevenson, Paul J.,Blain, Marine,Allen, Christopher C. R.
, p. 3020 - 3029 (2013/07/26)
Enantiopure cis-dihydrodiol bacterial metabolites of substituted benzene substrates were used as precursors, in a chemoenzymatic synthesis of the corresponding benzene oxides and of a substituted oxepine, via dihydrobenzene oxide intermediates. A rapid total racemization of the substituted benzene 2,3-oxides was found to have occurred, via their oxepine valence tautomers, in accord with predictions and theoretical calculations. Reduction of a substituted arene oxide to yield a racemic arene hydrate was observed. Arene hydrates have also been synthesised, in enantiopure form, from the corresponding dihydroarene oxide or trans-bromoacetate precursors. Biotransformation of one arene hydrate enantiomer resulted in a toluene-dioxygenase catalysed cis-dihydroxylation to yield a benzene cis-triol metabolite. The Royal Society of Chemistry 2013.
Chemoenzymatic synthesis of arene oxides and trans-dihydrodiols from cis-dihydrodiols of monosubstituted benzenes
Boyd, Derek R.,Sharma, Narain D.,Dalton, Howard,Clarke, David A.
, p. 45 - 46 (2007/10/03)
cis-Dihydrodiol bacterial metabolites of monosubstituted benzenes are used in the chemoenzymatic synthesis of the corresponding arene oxide and trans-dihydrodiol mammalian metabolites.
