Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Patent
1992-03-06
1993-11-30
Robinson, Douglas W.
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Resolution of optical isomers or purification of organic...
435156, 435911, 435921, 435924, 435938, 435942, C12P 4100, C12P 722
Patent
active
052664856
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a method of manufacturing (-)-2-halo-1-(substituted phenyl) ethanol and (-)-substituted styrene oxide and more particularly to a method of efficiently manufacturing (-)-2-halo-1-(substituted phenyl) ethanol by bringing a microorganism into contact with 2-halo-1-(substituted phenyl) ethanone and to a method of manufacturing (-)-substituted styrene oxide efficiently through cyclization thereof under alkaline conditions.
These compounds are useful as materials for synthesis of drugs, agrichemicals et cetera requiring to be optically active.
BACKGROUND OF THE INVENTION
As to optically active (-)-2-halo-1-(substituted phenyl) ethanol, the present inventors have not yet seen any patent, report or the like relating to its manufacture. Meanwhile, as to optically active chloro-substituted styrene oxide, there is a report that 72-86% e.e. could be achieved by epoxidation of chloro-substituted styrene by means of Nocardia corallina (Keizo Furuhasi; Organic Synthetic Chemistry, 43, 162 (1987)). Another known method of synthesis thereof is by interphase moving reaction between chloro-substituted benzaldehyde and dimethyl sulfonium methylide, but this method is extremely poor in optical purity attainable (Hiroyuki Sawada; Japanese Laid-open Patent Publication No. 105024/1976.
After having made intensive studies for development of an efficient method of manufacturing optically active (-)-2-halo-1-(substituted phenyl) ethanol and (-)-substituted styrene oxide, the present inventors discovered existence of some microorganisms capable of asymmetrically reducing 2-halo-1-(substituted phenyl) ethanone stereospecifically and converting it into (-)-2-halo-1-(substituted phenyl) ethanol and thus completed the invention.
DISCLOSURE OF THE INVENTION
The first aspect of the present invention is to provide a method of bringing a 2-halo-1-(substituted phenyl) ethanone represented by a general formula [1] ##STR1## (where X represents a chlorine atom or a bromine atom and each of substitution groups R.sup.1, R.sup.2 and R.sup.3 represents a hydrogen atom, a chlorine atom, a fluorine atom, a methyl group or a methoxy group except cases where 3 substitution groups are all hydrogen atoms) into contact with a microorganism selected from those belonging to Ashbya genus, Brettanomyces genus, Candida genus, Cryptococcus genus, Geortrichum genus, Pichia genus, Rhodosporidium genus, Rhodotorula genus, Saccharomyces genus, Torulopsis genus or Trigonopsis genus capable of reducing it asymmetrically into (-)-2-halo-1-(substituted phenyl) ethanol represented by a general formula [[2] ##STR2## (where X and substitution groups R.sup.1, R.sup.2 and R.sup.3 are the same as in the general formula [1] and * indicates an asymmetric carbon atom) and thereby to prepare (-)-2-halo-1-(substituted phenyl) ethanol.
The second aspect of the invention is to provide a method of manufacturing (-)-substituted styrene oxide represented by a general formula [3] ##STR3## (where substitution groups R.sup.1, R.sup.2 and R.sup.3 are the same as in the general formula [1] and [2] and * indicates an asymmetric carbon atom) by cyclizing under alkaline conditions (-)-2-halo-1-(substation phenyl) ethanol represented by the general formula [2] ##STR4## (where X and substitution groups R.sup.1, R.sup.2 and R.sup.3 are the same as in the general formula [1] and * indicates an asymmetrical carbon atom).
OPTIMUM MODE OF EMBODYING THE INVENTION
The microorganism used in the present invention for asymmetrical reduction of 2-halo-1-(substituted phenyl) ethanone for conversion into (-)-2-halo-1-(substituted phenyl) ethanol can be found in the following way.
For example, 50 ml of A culture medium comprising 40 g of glucose, 3 g of yeast extract, 13 g of (NH.sub.4).sub.2 HPO.sub.4, 7 g of KH.sub.2 PO.sub.4, 0.8 g of MgSO.sub.4 7H.sub.2 O, 60 mg of ZnSO.sub.4 7H.sub.2 O, 90 mg of FeSO.sub.4 7H.sub.2 O, 5 mg of CuSO.sub.4 5H.sub.2 O, 10 mg of MnSO.sub.4.4H.sub.2 O and 0.1 g of NaCl (per liter) is put into a 500 ml Sakaguchi
REFERENCES:
patent: 4857488 (1989-08-01), Kutsuki et al.
Christen, M. et al., J. Chem. Soc., Chem. Commun. 1988: 264-266.
Hummel, W.; Appl. Microbiol. Biotechnol. 34:15-19 (1990).
Imuta, M.; J. Org. Chem. 45:3352-3355 (1980).
Jones, B.; Tetrahedron 42:3351-3403 (1986).
Hasegawa Junzo
Konishi Yuko
Maemoto Shunichi
Sawa Ikuo
Kanegafuchi Kagaku Kogyo & Kabushiki Kaisha
Robinson Douglas W.
Saucier S.
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