Sulfoxides of high enantiopurity from bacterial dioxygenase-catalysed oxidation

Abstract

Selected strains of the bacterium Pseudomonas putida (previously shown to effect dioxygenase-catalysed asymmetric cis-dihydroxylation of alkenes) have been found to yield chiral sulfoxides from the corresponding sulfides with a strong preference for the (R)or (S)-configurations but without evidence of sulfone formation; similar results obtained using an Escherichia coliclone (pKST11, containing the Tod C1 C2 B and A genes encoding toluene dioxygenase from P. putida NCIMB 1 1767) are again consistent with a stereoselective dioxygenase-catalysed su Ifoxidation.

Actions of a versatile fluorene-degrading bacterial isolate on polycyclic aromatic compounds?

“…It appears that all bacterial strains reported to dioxygenate and cleave one of the aromatic rings of dibenzothiophene can also catalyze the formation of S-oxidation products (29,31); in some of the cases the further oxidation of DBT-5-oxide to the DBT sulfone was also observed. It is tempting to implicate the arene dioxygenase(s) of strain F297 in these sulfoxygenation reactions (1,45); however, there is no direct evidence supporting that conclusion at the present time.…”

Recombinant Chlorobenzene Dioxygenase from Pseudomonas sp. P51: A Biocatalyst for Regioselective Oxidation of Aromatic Nitriles

“…[29,38,39] However, in most expression systems used so far, such as pDTG601, [40] pKST11, [41] pDTG141, [42] p1/1, [39] pLAC365, pTAC365, [43] and pTCB144, [14] the dioxygenase genes were cloned downstream of promoters such as the lac or tac promoter. Such promoters are known to be not tightly regulated and the leakiness of these regulatory systems have been shown before.…”

Pseudomonas

“…Unexpectedly, the toluene dioxygenase of P. putida NCIMB 11767 (EC 1.14.12.11) produces optically active sulfoxides (monooxygenase reaction) at high enantiomeric excess rather than the achiral sulfones (dioxygenase reaction) from sulfides (Allen et at., 1995). Baeyer-Villiger reactions.…”