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Biotransformation of substituted pyridines with dioxygenase-containing microorganisms
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Garrett, Mark D., Scott, Robin, Sheldrake, Gary N., Dalton, Howard and Goode, Paul (2006) Biotransformation of substituted pyridines with dioxygenase-containing microorganisms. ORGANIC & BIOMOLECULAR CHEMISTRY, 4 (14). pp. 2710-2715. doi:10.1039/b606113c ISSN 1477-0520.
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Official URL: http://dx.doi.org/10.1039/b606113c
Abstract
A series of 2-, 3- and 4-substituted pyridines was metabolised using the mutant soil bacterium Pseudomonas putida UV4 which contains a toluene dioxygenase ( TDO) enzyme. The regioselectivity of the biotransformation in each case was determined by the position of the substituent. 4-Alkylpyridines were hydroxylated exclusively on the ring to give the corresponding 4-substituted 3- hydroxypyridines, while 3- alkylpyridines were hydroxylated stereoselectively on C-1 of the alkyl group with no evidence of ring hydroxylation. 2-Alkylpyridines gave both ring and side-chain hydroxylation products. Choro- and bromo-substituted pyridines, and pyridine itself, while being poor substrates for P. putida UV4, were converted to some extent to the corresponding 3- hydroxypyridines. These unoptimised biotransformations are rare examples of the direct enzyme-catalysed oxidation of pyridine rings and provide a novel synthetic method for the preparation of substituted pyridinols. Evidence for the involvement of the same TDO enzyme in both ring and side-chain hydroxylation pathways was obtained using a recombinant strain of Escherichia coli (pKST11) containing a cloned gene for TDO. The observed stereoselectivity of the side-chain hydroxylation process in P. putida UV4 was complicated by the action of an alcohol dehydrogenase enzyme in the organism which slowly leads to epimerisation of the initial (R)-alcohol bioproducts by dehydrogenation to the corresponding ketones followed by stereoselective reduction to the (S)-alcohols.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | ||||
| Journal or Publication Title: | ORGANIC & BIOMOLECULAR CHEMISTRY | ||||
| Publisher: | ROYAL SOC CHEMISTRY | ||||
| ISSN: | 1477-0520 | ||||
| Official Date: | 2006 | ||||
| Dates: |
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| Volume: | 4 | ||||
| Number: | 14 | ||||
| Number of Pages: | 6 | ||||
| Page Range: | pp. 2710-2715 | ||||
| DOI: | 10.1039/b606113c | ||||
| Publication Status: | Published |
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