Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates
Data(s) |
2008
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Resumo |
cis-Dihydrodiol metabolites were obtained from dioxygenase-catalysed asymmetric dihydroxylations of. five monocyclic (azabiphenyl) and four tricyclic (azaphenanthrene) azaarene substrates. Enantiopurity values and absolute configuration assignments were determined using a combination of stereochemical correlation, X-ray crystallography and spectroscopy methods. The degree of regioselectivity found during cis-dihydroxylation of monocyclic azaarenes (2,3 bond >> 3,4 bond) and of tricyclic azaarenes (bay region > non-bay region bonds) was dependent on the type of dioxygenase used. The cis-dihydrodiol metabolite from an azaarene (3-phenylpyridine) was utilised in the chemoenzymatic synthesis of the corresponding trans-dihydrodiol. |
Identificador |
http://dx.doi.org/10.1039/b810235j http://www.scopus.com/inward/record.url?scp=58149184319&partnerID=8YFLogxK |
Idioma(s) |
eng |
Direitos |
info:eu-repo/semantics/restrictedAccess |
Fonte |
Boyd , D , Sharma , N , Coen , G P , Hempenstall , F , Ljubez , V , Malone , J , Allen , C & Hamilton , J 2008 , ' Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates ' Organic and Biomolecular Chemistry , vol 6 , no. 21 , pp. 3957-3966 . DOI: 10.1039/b810235j |
Palavras-Chave | #/dk/atira/pure/subjectarea/asjc/1300/1303 #Biochemistry #/dk/atira/pure/subjectarea/asjc/1600/1605 #Organic Chemistry #/dk/atira/pure/subjectarea/asjc/1600/1606 #Physical and Theoretical Chemistry #/dk/atira/pure/subjectarea/asjc/2700 #Medicine(all) |
Tipo |
article |