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

Christopher Allen, Derek Boyd, Christopher Hardacre, Narain Sharma, V. Berbarian

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)727-739
Number of pages13
JournalAdvanced Synthesis & Catalysis
Volume349
Issue number4-5
DOIs
Publication statusPublished - Mar 2007

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (miscellaneous)
  • Organic Chemistry

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