Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Patent
1993-10-27
1995-02-21
Marx, Irene
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Resolution of optical isomers or purification of organic...
435911, 435156, 435931, 435872, 4352541, 4352551, 4352521, C12P 722, C12N 120, C12N 114
Patent
active
053914953
ABSTRACT:
The present invention concerns a process for the stereoselective enzymatic reduction of keto group-containing compounds such as N-(4-(2-chloroacetyl)phenyl)methanesulfonamido to form the corresponding hydroxyl-group containing compound. The process is selective for the D(+) enantiomer and is catalyzed by enzymes such as oxido-reductase or dehydrogense, or by microorganisms such as Hansenula, Rhodococcus, or Norcardia species.
REFERENCES:
patent: 3342584 (1967-09-01), Larsen et al.
patent: 4857468 (1989-08-01), Kutsuki et al.
patent: 5106736 (1992-04-01), Patel et al.
Bradshaw, et al. "A Pseudomonas sp. Alcohol Dehydrogenase With Broad Substrate Specificity and Unusual Stereospecificity for Organic Synthesis," J. Org. Chem., 57, 1526-1532, 1992.
Bradshaw, et al., "Lactobacillus kefir Alcohol Dehydrogenase: A Useful Catalyst for Synthesis," J. Org. Chem., 57, 1532-1536, 1992.
Larsen, A. A. and Lish, P. M., "A New Bio-Isostere: Alkylsulphonamidophenethanolamines," Nature, 203, 1283-1284, 1964.
Lok, K. P., et al., "Enzymes in Organic Synthesis. 34. Preparations of Enantiomerically Pure Exo- and Endo-Bridged Bicyclic [2.2.1] and [2.2.2] Chiral Lactones via Sterospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Meso Diols," J. Am. Chem. Soc. 107(8), 2521-2526, 1985.
Ng. G. S. Y, et al., "Enzymes in Organic Synthesis-29. Preparations of Enantiomerically Pure cis-2,3- and 2,4-Dimethyl Lactones via Horse Liver Alcohol Dehydrogenase-catalyzed Oxidations," Tetrahedron 40(8), 1235-1243, 1984.
Bridges, A. J. et al., "Preparations of Enantiomerically Pure Bicyclic [3.2.1] and [3.3.1] Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Meso Diols," J. Am. Chem. Soc. 106(5), 1461-1467, 1984.
Fischli, A., "Chiral Building Blocks in Enantiomer Synthesis Using Enzymatic Transformations," Mod. Synth. Methods, Conf. Pap. Int. Semin., 2nd., Rolf Scheffold (Ed), 269-350, 1980.
Lish, et al., "Pharmacological and toxicological Properties of Two New .beta.-Adrenergic Receptor Antagonists," J. Pharma. Exper. Ther., 149, 161-173, 1965.
Somani, P. and Bachand, T., "Blockade of Cardiac Effects of Isoproterenol by the Stereoisomers of Sotalol," European Journal of Pharmacology, 7, 239-247, 1969.
Akita, H., et al., "The Use of Microorganisms in Organic Synthesis.IV. Microbiological Asymmetric Reduction of Methyl 3-Phenyl 2-Oxybutyrate," Chem. Pharm. Bull. 32(4), 1342-1348, 1984.
Hummel, W., "Enzyme-catalyzed Synthesis of Optically Pure R(+)-phenylethanol," Biotechnol. Lett. 12(6), 403-408, 1990.
Hummel, et al., "New Enzymes for the Synthesis of Chiral Compounds," Ann. N.Y. Acad. Sci., 434, 194-205, 1984.
Whitlock, H. W., Jr., "Enzymatic Versus Chemical Synthesis of Molecules Labeled with Heavy Isotopes," Tech. Chem. (N.Y.), 10, 1045-1065, 1976.
Whitesides, et al., "The Use of Enzymes as Catalysts for Synthesis in Medicinal Chemistry: Chiral Synthons and Carbohydrates," New Methods in Drug Research, 2, 1-15, 1988.
Flynn, G. A. and Beight, D. W., "An Efficient Synthesis of Ethyl (R)-2-Hydroxy-4-Phenylbutyrate: A Useful Intermediate in the Synthesis of Converting Enzyme Inhibitors," Tetrahedron Lett. 29(4), 423-426, 1988.
Fuganti, C. and Servi, S., "Enzyme Mediated Synthesis of Pheromones," Bioflavour '87, Proc. Int. Conf., Peter Schreier (Ed), 555-569, 1988.
Sonnet, P. E., "Enzymes for Chiral Synthesis," Chemtech, 18(2), 94-98, 1988.
Dodds, et al., "Enzymes in Organic Synthesis. 38. Preparations of Enantiometerically Pure Chiral Hydroxydecalones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Reductions of Decalindiones," J. Am. Chem. Soc. 110(2), 577-583, 1988.
Battersby, A. R., "Enzymic Synthesis of Labeled Chiral Substances," Ciba Found. Symp., 111, 22-30, 1985.
Banerjee Amit
McNamee Clyde G.
Patel Ramesh N.
Szarka Laszlo J.
Bristol--Myers Squibb Company
Marx Irene
Savitsky Thomas R.
LandOfFree
Stereoselective reduction of ketones does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Stereoselective reduction of ketones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Stereoselective reduction of ketones will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1929404