Whole-cell biotransformation of m-ethyltoluene into 1S,6R-5-ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid as an approach to the C-ring of the binary indole-indoline alkaloid vinblastine

Martin G. Banwell*, Alison J. Edwards, David W. Lupton, Gregg White

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    17 Citations (Scopus)

    Abstract

    The title compound 3, a potential building block for the construction of analogues of the clinically important anticancer agent vinblastine (1), has been prepared in an efficient manner through a whole-cell biotransformation of m-ethyltoluene (4) using the microorganism Pseudomonas putida BGXM1 which expresses the enzyme toluate dioxygenase (TADO). Metabolite 3 was readily converted into derivatives 5-8 using conventional chemical techniques and the structure, including absolute stereochemistry, of the last of these was established by single-crystal X-ray analysis.

    Original languageEnglish
    Pages (from-to)14-17
    Number of pages4
    JournalAustralian Journal of Chemistry
    Volume58
    Issue number1
    DOIs
    Publication statusPublished - 2005

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