A comparative study of the synthesis of 3-substituted catechols using an enzymatic and a chemoenzymatic method
Data(s) |
01/03/2007
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Resumo |
A series of cis-dihydrodiol metabolites, available from the bacterial dioxygenase-catalysed oxidation of monosubstituted benzene substrates using Pseudomonas putida UV4, have been converted to the corresponding catechols using both a heterogeneous catalyst (Pd/C) and a naphthalene cis-diol dehydrogenase enzyme present in whole cells of the recombinant strain Escherichia coli DH5 alpha(pUC129: nar B). A comparative study of the merits of both routes to 3-substituted catechols has been carried out and the two methods have been found to be complementary. A similarity in mechanism for catechol formation under both enzymatic and chemoenzymatic conditions, involving regioselective oxidation of the hydroxyl group at C-1, has been found using deuterium labelled toluene cis-dihydrodiols. The potential, of combining a biocatalytic step (dioxygenase-catalysed cis-dihydroxylation) with a chemocatalytic step (Pd/C-catalysed dehydrogenation), into a one-pot route to catechols, from the parent substituted benzene substrates, has been realised. |
Identificador |
http://dx.doi.org/10.1002/adsc.200600437 http://www.scopus.com/inward/record.url?scp=34547178923&partnerID=8YFLogxK |
Idioma(s) |
eng |
Direitos |
info:eu-repo/semantics/restrictedAccess |
Fonte |
Allen , C , Boyd , D , Hardacre , C , Sharma , N & Berbarian , V 2007 , ' A comparative study of the synthesis of 3-substituted catechols using an enzymatic and a chemoenzymatic method ' Advanced Synthesis & Catalysis , vol 349 , no. 4-5 , pp. 727-739 . DOI: 10.1002/adsc.200600437 |
Palavras-Chave | #/dk/atira/pure/subjectarea/asjc/1500/1503 #Catalysis #/dk/atira/pure/subjectarea/asjc/1600/1601 #Chemistry (miscellaneous) #/dk/atira/pure/subjectarea/asjc/1600/1605 #Organic Chemistry |
Tipo |
article |