Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Patent
1992-04-07
1994-10-18
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...
435822, 435911, C12P 4100
Patent
active
053568125
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is the national stage of international application PCT/JP91/01064 filed Aug. 9th, 1991, and claims priority to Japanese Application No. 211861/1990 filed August 10th, 1990, Japanese Application No. 276101/1990 filed Oct. 15th, 1991, and Japanese Application No. 643454/1991 filed Jul. 4th, 1991, the specifications of which are hereby incorporated by reference.
DESCRIPTION
Technical Field
The present invention relates to a process for producing optically active 3-phenyl-1,3-propanediol. More particularly, the invention relates to a process for producing optically active 3-phenyl-1,3-propanediol characterized by permitting a microorganism or a preparation thereof to act on a mixture of enantiomers of 3-phenyl-1,3-propanediol and harvesting the residual optically active 3-phenyl-1,3-propanediol.
Optically active 3-phenyl-1,3-propanediol is an important intermediate for the synthesis of various medicinal compounds.
Background Art
For the production of optically active 3-phenyl-1,3-propanediol, there is known a position-selective chemical reduction of 2,3-epoxycinnamyl alcohol [J. Org. Chem., 53(17), 4081 (1988)] as well as a chemical reduction of optically active 3-phenyl-3-hydroxypropionic acid [Tetrahedron Lett., 26(3), 351 (1985) and U.S. Pat. No. 4921797].
However, the former process is not fully satisfactory in position selectivity and in terms of chemical purity. The latter process is also disadvantageous in that the optically active organic acid must be resolved with an optical resolution reagent beforehand and that the optical purity of the product optically active compound is low.
Under the circumstances, the establishment of an economical and expedient process for production of optically active 3-phenyl-1,3-propanediol of high optical purity has been demanded.
DISCLOSURE OF INVENTION
It is an object of the present invention to provide a process for producing optically active 3-phenyl-1,3-propanediol of high optical purity expediently and efficiently with the aid of a microorganism.
It is another object of the invention to provide a commercially useful process for producing optically active 3-phenyl-1, 3-propanediol.
It is a further object of the invention to provide an efficient process for producing (R)-3-phenyl-1, 3propanediol or (S)-3-phenyl-1,3-propanediol with the aid of a microorganism.
The present inventors were interested in the utilization of a microorganism for the economical and expedient production of optically active 3-phenyl-1,3-propanediol of high optical purity and performed an extensive screening of microorganisms, mostly isolates from the soil, to find strains suited for the above purpose. As a consequence, they discovered that certain strains selected from certain genera and species of microorganisms act on a mixture of enantiomers of 3-phenyl-1,3-propanediol to leave either (R)-3-phenyl-1,3-propanediol or (S)-3-phenyl-1,3-propanediol. The present invention has been accomplished on the basis of the above finding.
The microorganisms to be employed in accordance with the invention may be any strain of microorganism that is able to act on a mixture of enantiomers of 3-phenyl-1,3-propanediol to leave either (R)-3-phenyl-1,3-propanediol or (S)-3-phenyl-1, 3-propanediol.
The genera of those microorganisms which leave (R)-3-phenyl-1,3-propanediol include, among others, Candida, Hansenula, Rhodotorula, Protaminobacter, Aspergillus, Alternaria, Macrophomina, Preussia and Talaromyces.
The genera of those microorganisms which leave (S)-3-phenyl-1,3-propanediol include, among others, Candida, Geotrichum, Leucosporidium, Pichia, Torulaspora, Trichosporon, Escherichia, Micrococcus, Corynebacterium, Gordona, Rhodococcus, Aspergillus, Emericella, Absidia, Fusarium, Dactyllure, Serratia and Pseudomonas.
Such a microorganism is generally grown in a culture medium and, then, submitted to the reaction with a mixture of enantiomers of 3-phenyl-1,3-propanediol. A preparation of such microorganism may instead be used in the reaction wit
REFERENCES:
patent: 4921798 (1990-05-01), Boaz
Chemical Abstracts, vol. 117, No. 1, Jul. 6, 1992 Columbus, Ohio, US; abstract No. 6149m, Akikazu Matsuyama et al. "Manufacture of optically active 3-phenyl-1,3-propanediol with bacteria".
Chemical Abstracts, vol. 117, No. 17, Oct. 26, 1992, Columbus, Ohio, US; abstract No. 169594s, Kazumasa Otsubo et al. "Manufacture of optically active 1,3-propanediols".
Chemical Abstracts, vol. 118, No. 11, Mar. 15, 1993, Columbus, Ohio, US; abstract No. 100550c, Kazumasa Otsubo et al. "Manufacture of (S)-3-phenyl-3-propanols from racemic 3-phenyl-3-propanols with microorganisms".
Ito Michio
Kawada Naoki
Kobayashi Yoshinori
Matsuyama Akinobu
Daicel Chemical Industries Ltd.
Marx Irene
Saucier S.
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