Enzyme-catalysed oxidation of 1,2-disulfides to yield chiral thiosulfinate, sulfoxide and cis-dihydrodiol metabolites


Autoria(s): Boyd, Derek R.; Sharma, Narain D.; Shepherd, Steven D.; Allenmark, Stig G.; Allen, Christopher C R
Data(s)

2014

Resumo

Enantioenriched and enantiopure thiosulfinates were obtained by asymmetric sulfoxidation of cyclic 1,2-disulfides, using chemical and enzymatic (peroxidase, monooxygenase, dioxygenase) oxidation methods and chiral stationary phase HPLC resolution of racemic thiosulfinates. Enantiomeric excess values, absolute configurations and configurational stabilities of chiral thiosulfinates were determined. Methyl phenyl sulfoxide, benzo[c]thiophene cis-4,5-dihydrodiol and 1,3-dihydrobenzo[c]thiophene derivatives were among unexpected types of metabolites isolated, when acyclic and cyclic 1,2-disulfide were used as substrates for Pseudomonas putida strains. Possible biosynthetic pathways are presented for the production of metabolites from 1,4-dihydrobenzo-2,3-dithiane, including a novel cis-dihydrodiol metabolite that was also derived from benzo[c]thiophene and 1,3-dihydrobenzo[c]thiophene.

Identificador

http://pure.qub.ac.uk/portal/en/publications/enzymecatalysed-oxidation-of-12disulfides-to-yield-chiral-thiosulfinate-sulfoxide-and-cisdihydrodiol-metabolites(e3599827-f09a-4c3a-8391-cddb87f55263).html

http://dx.doi.org/10.1039/c4ra02923b

http://www.scopus.com/inward/record.url?scp=84903642447&partnerID=8YFLogxK

Idioma(s)

eng

Direitos

info:eu-repo/semantics/restrictedAccess

Fonte

Boyd , D R , Sharma , N D , Shepherd , S D , Allenmark , S G & Allen , C C R 2014 , ' Enzyme-catalysed oxidation of 1,2-disulfides to yield chiral thiosulfinate, sulfoxide and cis-dihydrodiol metabolites ' RSC Advances , vol 4 , no. 52 , pp. 27607-27619 . DOI: 10.1039/c4ra02923b

Palavras-Chave #/dk/atira/pure/subjectarea/asjc/1500 #Chemical Engineering(all) #/dk/atira/pure/subjectarea/asjc/1600 #Chemistry(all)
Tipo

article