138769-97-8Relevant articles and documents
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
Enzymatic oxidation of thioanisoles: Isolation and absolute configuration of metabolites
Finn, Kevin J.,Cankar, Petr,Jones, Timothy R.B.,Hudlicky, Tomas
, p. 2833 - 2836 (2007/10/03)
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
Toluene and naphthalene dioxygenase-catalysed sulfoxidation of alkyl aryl sulfides
Boyd, Derek R.,Sharma, Narain D.,Haughey, Simon A.,Kennedy, Martina A.,McMurray, Brian T.,Sheldrake, Gary N.,Allen, Christopher C. R.,Dalton, Howard,Sproule, Kenneth
, p. 1929 - 1933 (2007/10/03)
A series of alkyl aryl sulfides were metabolised, using selected strains of the soil bacterium Pseudomonas putida containing either toluene dioxygenase (TDO) or naphthalene dioxygenase (NDO), to give chiral sulfoxides. Alkyl aryl sulfoxides 2a-2k, 4a-4j and 4l, having enantiomeric excess (ee) values of >90%, were obtained by use of the appropriate strain of P. putida (UV4 or NCIMB 8859). Enantiocomplementarity was observed for the formation of sulfoxides 2a, 2b, 2d, 2j, 4a, 4b and 4d, with TDO-catalysed (UV4) oxidation favouring the (R) enantiomer and NDO-catalysed oxidation (NCIMB 8859) the (S) enantiomer. Evidence of involvement of the TDO enzyme was obtained using a recombinant strain of Escherichia coli (pKST 11). The marked degree of stereoselectivity appears to be mainly due to enzyme-catalysed asymmetric sulfoxidation, however the possibility of a minor contribution from kinetic resolution, in some cases, cannot be excluded.