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Issue 14, 2006
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Biotransformation of substituted pyridines with dioxygenase-containing microorganisms

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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.

Graphical abstract: Biotransformation of substituted pyridines with dioxygenase-containing microorganisms

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Publication details

The article was received on 02 May 2006, accepted on 24 May 2006 and first published on 07 Jun 2006


Article type: Paper
DOI: 10.1039/B606113C
Citation: Org. Biomol. Chem., 2006,4, 2710-2715

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    Biotransformation of substituted pyridines with dioxygenase-containing microorganisms

    M. D. Garrett, R. Scott, G. N. Sheldrake, H. Dalton and P. Goode, Org. Biomol. Chem., 2006, 4, 2710
    DOI: 10.1039/B606113C

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