A comparative study of the synthesis of 3-substituted catechols using an enzymatic and a chemoenzymatic method


Autoria(s): Allen, Christopher; Boyd, Derek; Hardacre, Christopher; Sharma, Narain; Berbarian, V.
Data(s)

01/03/2007

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://pure.qub.ac.uk/portal/en/publications/a-comparative-study-of-the-synthesis-of-3substituted-catechols-using-an-enzymatic-and-a-chemoenzymatic-method(85e1a5d3-c0e9-4d4f-9835-3dfe722cee4c).html

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