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Titolo:
TOLUENE AND NAPHTHALENE DIOXYGENASE-CATALYZED SULFOXIDATION OF ALKYL ARYL SULFIDES
Autore:
BOYD DR; SHARMA ND; HAUGHEY SA; KENNEDY MA; MCMURRAY BT; SHELDRAKE GN; ALLEN CCR; DALTON H; SPROULE K;
Indirizzi:
QUEENS UNIV BELFAST,SCH CHEM BELFAST BT9 5AG ANTRIM NORTH IRELAND QUEENS UNIV BELFAST,QUESTOR CTR BELFAST BT9 5AG ANTRIM NORTH IRELAND UNIV WARWICK,DEPT BIOL SCI COVENTRY CV4 7AL W MIDLANDS ENGLAND
Titolo Testata:
Journal of the Chemical Society. Perkin transactions. I (Print)
fascicolo: 12, , anno: 1998,
pagine: 1929 - 1933
SICI:
0300-922X(1998):12<1929:TANDSO>2.0.ZU;2-3
Fonte:
ISI
Lingua:
ENG
Soggetto:
CYCLOHEXANONE MONOOXYGENASE; ASYMMETRIC OXIDATION; MICROBIAL OXIDATION; ABSOLUTE-CONFIGURATION; BACTERIAL METABOLISM; ENZYMATIC OXIDATION; CHIRAL SULFOXIDES; ORGANIC SULFIDES; BIOTRANSFORMATION; STEREOSELECTIVITY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
54
Recensione:
Indirizzi per estratti:
Citazione:
D.R. Boyd et al., "TOLUENE AND NAPHTHALENE DIOXYGENASE-CATALYZED SULFOXIDATION OF ALKYL ARYL SULFIDES", Journal of the Chemical Society. Perkin transactions. I (Print), (12), 1998, pp. 1929-1933

Abstract

A series of alkyl aryl sulfides were metabolised, using selected strains of the soil bacterium Pseudomonas putida containing either toluenedioxygenase (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 appropriatestrain of P. putida (UV4 or NCIMB 8859), Enantiocomplimentarity 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 ofEscherichia 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.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 20:13:46