Whole-Cell Biotransformation of m -Ethyltoluene into 1 S ,6 R -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.
Date
2005
Authors
Banwell, Martin
Edwards, Alison
Lupton, David
Whited, Gregg
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CSIRO Publishing
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.
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Keywords: Biological organs; Carboxylic acids; Catalysis; Crystal structure; Enzymes; Hydrocarbons; Microorganisms; Molecular structure; Single crystals; Synthesis (chemical); Tumors; X ray analysis; Bromolactonization; Indole; Indoline ring system; Whole-cell biot
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Source
Australian Journal of Chemistry
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Journal article
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2037-12-31
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