777094-95-8Relevant academic research and scientific papers
Enzymatic oxidation of thioanisoles: Isolation and absolute configuration of metabolites
Finn, Kevin J.,Cankar, Petr,Jones, Timothy R.B.,Hudlicky, Tomas
, p. 2833 - 2836 (2004)
Oxidation of p-bromothioanisole with toluene dioxygenase provides the corresponding diene diol 2 in good yield. Electrochemical reduction of 2 gives access to diene diol 3, which is not accessible by direct bio-oxidation of thioanisole. Absolute configura
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.
Toluene dioxygenase-mediated oxidation of bromo(methylsulfanyl)benzenes. Absolute configuration of metabolites and evaluation of chemo- and regioselectivity trends
Finn, Kevin J.,Pavlyuk, Oksana,Hudlicky, Tomas
, p. 1709 - 1726 (2007/10/03)
A series of 2-, 3-, and 4-bromo-1-(methylsulfanyl)benzenes was subjected to whole-cell fermentation with Escherichia coli JM 109 (pDTG601), a recombinant strain that expresses toluene dioxygenase. New metabolites were isolated and their structure and abso
