PREPARATION OF OPTICALLY ACTIVE ESTER

    公开(公告)号:JPS59220194A

    公开(公告)日:1984-12-11

    申请号:JP9447083

    申请日:1983-05-27

    Abstract: PURPOSE:To prepare an optically active ester useful as an insecticidal component, in high optical purity, economically in an industrial scale, by using a microbial asymmetric hydrolysis, etc. CONSTITUTION:The ester of formula IV (A is H, alkyl, etc.) is subjected to the asymmetric hydrolysis with an esterase produced by a microorganism belonging to Arthrobacter genus and capable of asymmetrically hydrolyzing said ester to obtain a mixture of an optically active alcohol of formula III (* is asymmetric carbon atom) and the ester of the antipode of said alcohol. The mixture is made to react with the carboxylic acid halide of formula II (R is substituted cyclopropyl, substituted benzyl, etc.) in the presence of an acid acceptor to acylate the optically active alcohol of formula III, and the optically active ester of formula I (R and * are same as defined above) is separated from the resultant reaction mixture.

    BIOCHEMICAL PREPARATION OF (S)-(-)-ALPHA-CYANO-3-PHENOXYBENZYL ALCOHOL

    公开(公告)号:JPS5894389A

    公开(公告)日:1983-06-04

    申请号:JP19134081

    申请日:1981-11-28

    Abstract: PURPOSE:To prepare the titled compound having high optical purity, by a biochemical means, by asymmetrically hydrolyzing the carboxylic acid ester of (R,S)-alpha-cyano-3-phenoxybenzyl alcohol with a specific esterase. CONSTITUTION:An organic carboxylic acid[1-18C (un)saturated carboxylic acid]ester of (R,S)-alpha-cyano-3-phenoxybenzyl alcohol is asymmetrically hydrolyzed with an esterase produced by microorganisms belonging to Arthrobacter, Alcaligenes, Achromobacter, Pseudomonas, Aspergillus, or Mucor genus or an esterase derived from the pancreas of an animal and capable of asymmetrically hydrolyzing said ester. The ester is resolved by this process into (S)-(-)-alpha-cyano- 3-phenoxy-benzyl alcohol and its enantiomorphic ester, from which the titled compound is separated. The S-isomer has much stronger insecticidal activity than R-isomer.

    BIOCHEMICAL OPTICAL RESOLUTION OF CYCLOPENTENOLONE DERIVATIVE

    公开(公告)号:JPS5847495A

    公开(公告)日:1983-03-19

    申请号:JP14687981

    申请日:1981-09-16

    Abstract: PURPOSE:Optical resolution wherein esterase produced by a bacterium or esterase of animal pancreas is reacted with the titled substance, the prepared substance is hydrolyzed asymmetrically and divided into an optical active cyclopentenone and an ester. CONSTITUTION:Esterase produced by a bacterium belonging to the genus Enterobacter, Arthrobacter, etc. or esterase of animal pancreas is reacted with an organic carboxylic acid (1-18 C) ester of (+ or -)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone. An aqueous solution containing raw esterase, extracted solution of esterase, etc. is reacted with an ester of cyclopentenone shown by the formula with stirring, asymmetric hydrolysis is carried out, and liberated optical active propynylcyclopentenolone is separated from an unreacted antipode ester and they are recovered.

    PRODUCTION OF (S)-AMINO COMPOUND
    18.
    发明专利

    公开(公告)号:JP2001008696A

    公开(公告)日:2001-01-16

    申请号:JP18367399

    申请日:1999-06-29

    Abstract: PROBLEM TO BE SOLVED: To stereoselectively obtain the subject (S)-amino compound that is useful as an intermediate for medicines, agrochemicals and the like and as a basic reagent for optical resolution by allowing a specific microorganism in Arthrobacter or the like to act on a specific ketone in the present of an amine. SOLUTION: A microorganism in Arthrobacter, capable of stereoselectively producing an (S)-amine represented by formula II by acting on a ketone represented by formula I (R1 is a 1-5C alkyl; X is a phenyl which may be substituted, a naphthyl group which may be substituted; n is an integer of 0-4), or a treated product of the microorganism, is allowed to act on the above-cited ketone (for example, acetophenone) in the presence of an amine, to obtain the objective (S)-amino compound [for example, (S)-1-phenylethylamine] that is useful as an intermediate for medicines, agrochemicals or an basic reagent for optical resolution.

    ESTERASE GENE AND ITS USE
    19.
    发明专利

    公开(公告)号:JPH10210974A

    公开(公告)日:1998-08-11

    申请号:JP34407596

    申请日:1996-12-24

    Abstract: PROBLEM TO BE SOLVED: To obtain the subject gene which codes esterase capable of asymmetrically hydrolyzing an organocarboxylic ester of a cyclopentenolone as an important intermediate for medicines and aglochemicals and is intended for production of microorganisms capable of producing excellent esterase useful for separating/ producing an S type enantiomorph of cyclopentenolones advantageously even on an industrial scale. SOLUTION: This esterase gene codes esterase having the ability to produce an S type enantiomorph of a cyclopentenolone by asymmetric hydrolysis of an organocarboxylic ester of a cyclopentenolone shown by formula I (R1 is a 1-10C alkyl, 2-10C alkenyl or the like), and capable of hybridizing it to a base sequence shown by formula II. It can be obtained by the PCR method which uses chromosome DNA of a Burkholderia microorganism as the template.

    METHOD FOR IMMOBILIZING MICROORGANISM

    公开(公告)号:JPH08103274A

    公开(公告)日:1996-04-23

    申请号:JP24288094

    申请日:1994-10-06

    Abstract: PURPOSE: To uniformly immobilize a microorganism in good yield without deteriorating enzymic activities by dispersing an aqueous solution of a water-soluble monomer and a water-soluble crosslinking agent containing the microorganism suspended therein in the presence of a water-soluble polymer in a hydrophobic liquid and carrying out the water-in-oil type suspension copolymerization. CONSTITUTION: An aqueous solution of a water-soluble unsaturated monomer (e.g. acrylamide) and a water-soluble unsaturated monomer capable of crosslinking the monomer (e.g. N,N'-methylenebisacrylamide) containing a microorganism [e.g. Agrobacterium radiobacter SC-C15-1 (FERM P-3843)] suspended therein is dispersed in the presence of a water-soluble polymer containing the water-soluble unsaturated monomer as a component (e.g. a water-soluble acrylamide polymer) in a hydrophobic liquid (e.g. n-heptane) and the water-in-oil type suspension copolymerization of both the water-soluble unsaturated monomer with the water-soluble unsaturated monomer capable of crosslinking the monomer is then carried out. Thereby the microorganism is stably and uniformly immobilized in the interior of particles insoluble in water in good yield without deteriorating enzymic activities of the microorganism.

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