Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Patent
1993-08-05
1995-10-17
Knode, Marian C.
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Resolution of optical isomers or purification of organic...
4352521, 435823, 435830, 435875, 435940, C12P 4100, C12N 120
Patent
active
054590671
DESCRIPTION:
BRIEF SUMMARY
TITLE OF INVENTION
A method for producing optically active norborneol this application is a 371 of PCT/JP92/01588 filed Dec. 4, 1992.
TECHNICAL FIELD
The present invention relates to a method for producing optically active norborneol by treating exonorbornane type ester with a microorganism.
BACKGROUND ART
Among methods for producing norborneol, the following chemical synthesis method is known: Norbornane as starting material is reacted with an organic acid to form an ester of norbornane; and then, this ester is chemically deacetylated to obtain norborneol. According to such a chemical synthesis method, four kinds of stereoisomers ((+, -)-(endo, exo)-norborneol) are generated, so that complicated purification steps are required for obtaining optically active norborneol by chemical synthesis.
As a method for biologically producing norborneol, the following method is known: An ester of norbornane is brought into contact with a microorganism or reacted with an enzyme and the ester is hydrolyzed. In recent years, Th. Oberhauser et. al. reported a method for producing (-)-norborneol from (+)-norbornyl acetate by using lipass derived from Candida cylindraceae (Th. Oberhauser et. al., Tetrahedron, 43, 3931-3944 1987). Moreover, Oritani et. al. reported a method for producing (-)bornsol and (-)isoborneol from (.+-.)bornyl acetate and (.+-.)isobornyl acetate by using a culture of Trichoderma sp, Trichoderma koningi, Bacillus subtilis var. Niger, and Absidia hyalospora (T. Oritani et. al., Agr. Biol. Chemo, 38(10), 1961-1964, 1974). However, the reactions have low selectivity and thus obtained products have low optical purity. Japanese Laid-Open Patent Publication No. 2-273196 discloses an optical resolution method in which an inhibitor, for selectively inhibiting the reaction of one of the enantiomers by a biological catalyst, resolves a racemic compound. This method can be used for preparing optically active norborneol. However, this method has the following disadvantages: screening is required in order to obtain an inhibitor effective for the selection of optically active norborneol; and an inhibitor should be removed in the course of purification after the reaction, thus complicated manipulation is required. In view of these circumstances, there has been a demand for an improved biological method for obtaining optically active norborneol, in which an ester is brought into contact with a microorganism or enzyme with high stereoselectivity in the course of the hydrolysis of the ester.
DISCLOSURE OF INVENTION
According to the present invention, a method for producing optically active norborneol with high purity by treating an exo-norbornane type ester with a microorganism is provided.
A method for producing an optically active norborneol of the present invention includes the step of bringing a microorganism or treated cells thereof into contact with (.+-.)-exo-norbornane type ester represented by Formula (I): ##STR1##
where R represents an acyl group, A and B represent independently hydrogen or A and B are taken together to form a chemical bond, genus Pseudomonas, the genus Acetobacter, the genus Arthrobacter, the genus Rhodotorula, and the genus Saccharomyces.
According to the present invention, (2S)-exo-norbornane type ester is selectively hydrolyzed by bringing (.+-.)-exo-norbornane type esters represented by the above-mentioned Formula (I) into contact with the above-mentioned microorganisms or treated cells thereof. Due to this hydrolysis, optically active alcohol and unchanged (2R)-exo-norbornane type ester are obtained.
According to the above-mentioned method, exo-norbornane type alcohol or (2R)-exo-norbornane type ester is obtained from the reaction solution. represented by Formula (I): ##STR2##
where R represents an acyl group, A and B represent independently hydrogen or A and B are taken together to form a chemical bond.
In Formula (I), the acyl group is an aliphatic acyl group with 2 to 10 carbon atoms, and preferably an aliphatic acyl group with 2 to 7 carbon atoms. Examples of the aliphatic a
REFERENCES:
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Irwin, A. J., et al., "Stereoselective Horse Liver Alcohol Dehydrogenase Catalyzed Oxidoreductions of Some Bicyclic [2.2.1] and [3.2.1] Ketones and Alcohols", J. Am. Chem. Soc., 98, pp. 8476-8481 (1976).
Kazlauskas, R. J., et al., "A Rule to Predict Which Enantiomer of a Secondary Alcohol Reacts Faster in Reactions Catalyzed by Cholesterol Esterase, Lipase from Pseudomonas cepacia, and Lipase from Candida rugosa", J. Org. Chem., 56, pp. 2656-5665 (1991).
Narisada, M., et al., "Synthesis and In Vitro Activity of Various Derivatives of a Novel Thromboxane Receptor Antagonist, (.+-.)-(5Z)-7-[3-endo-(Phenylsulfonyl)amino]bicyclo[2.2.1]hept-2-exo-yl]he ptenoic Acid", J. Med. Chem., 31, pp. 1847-1854 (1988).
Oberhauser, T., et al., "Enzymatic Resolution of Norbornane-Type Esters", Tetrahedron, 43, pp. 3931-3944 (1987).
Oritani, T., et al., "Microbial Resolution of (.+-.)-Borneols", Agr. Biol. Chem., 38, pp. 1961-1964 (1974).
Rabiller, C. G., et al., "Enzymatic Recognition of Diastereomeric Esters", Tetrahedron, 46, pp. 4231-4240 (1990).
Kageyama Bunji
Kawata Kyozo
Nakae Masanori
Sonoyama Takayasu
Haley, Jr. James F.
Hansbro Kevin R.
Knode Marian C.
Saucier S.
Shionogi Seiyaku Kabushiki Kaisha
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