Garrett, Mark D.; Scott, Robin; Sheldrake, Gary N.; Dalton, Howard; Goode, Paul published the artcile< Biotransformation of substituted pyridines with dioxygenase-containing microorganisms>, Product Details of C5H4ClNO, the main research area is toluene dioxygenase substituted pyridine oxidation.
A series of 2-, 3- and 4-substituted pyridines was metabolized 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. Chloro- 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 unoptimized biotransformations are rare examples of the direct enzyme-catalyzed 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 alc. dehydrogenase enzyme in the organism which slowly leads to epimerization of the initial (R)-alc. bioproducts by dehydrogenation to the corresponding ketones followed by stereoselective reduction to the (S)-alcs.
Organic & Biomolecular Chemistry published new progress about Oxidation, regioselective. 96630-88-5 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, Product Details of C5H4ClNO.