Daicel Chemical Industries, Ltd.

Teruyuki Nikaido

Akinobu Matsuyama

Yoshinori Kobayashi

Yoichiro Ueda

Takeshi Hamatani

Naoki Kawada

D-amino acid with high optical purity represented by formula (1-A) and/or formula (1-B), ##STR1## wherein R represents H or OH, ##STR2## wherein R.sub.1, R.sub.2 each represents H or OH, and amine represented by formula (2-A) and/or formula (2-B) ##STR3## wherein R represents H or OH, ##STR4## wherein R.sub.1 and R.sub.2 each represents H or OH, can be produced economically in an industrial scale by contacting a mixture of enantiomers of amino acid represented by the above formula (1-A) and/or formula (1-B) with a microorganism capable of selectively degrading L-amino acid or with at least one of the treated products of the microorganism.

Method of producing D-amino acid and method of producing amine

Tyrosine decarboxylase, or microorganisms of the genuses Enterococcus, Lactobacillus, Providencia, Fusarium, and Gibberella were reacted with a mixture of the enantiomers of threo-3-phenylserine or its halogen substitution products to produce (R)-2-amino-1-phenylethanol or its halogen substitution products. At the same time, one of the enantiomers of threo-3-phenylserine or its halogen substitution products were selectively left, and optically active threo-3-phenylserine or its halogen substitution products were produced. In addition, a novel material of 3-(3-chlorophenyl)serine, which is a substrate of the reaction in the present invention, was produced. (R)-2-amino-1-phenylethanol or its halogen substitution products, and optically active threo-3-phenylserine or its halogen substitution products can economically be produced on an industrial scale.

3-(3-chlorophenyl) serine

Method of producing (R)-2-amino-1-phenylethanol and opticaly active

Method of producing (R)-2-amino-1-phenylethanol and optically active

An optically active 1,3-butanediol can be produced by either (1) treating a mixture of 1,3-butanediol enantiomers with a microorganism, which has been optionally treated, capable of asymmetrically assimilating said mixture, or (2) preparing a microorganism, which has been optionally treated, capable of asymmetrically reducing 4-hydroxy-2-butanone, and collecting optically active 1,3-butanediol.

Process for producing optically active 1,3-butanediol by reduction of

Process for producing optically active 1,3-butanediol by asymmetric

An optically active 2-hydroxy acid derivative is produced by treating a 2-oxo acid derivative with a microorganism, which has been optionally treated, capable of asymmetrically reducing said 2-oxo acid derivative into an optically active (R)- or (S)-2-hydroxy acid derivative represented by the formula (II) and recovering the optically active (R)- or (S)-hydroxy acid derivative thus formed. Optically active 2-hydroxy acid derivatives are important intermediates in the synthesis of various drugs such as a remedy for hypertension.

Process for the production of optically active 2-hydroxy acid esters

2-Oxo-4-phenylbutyric acid is treated with a microorganism, which has been optionally treated, capable of asymmetrically reducing 2-oxo-4-phenylbutyric acid into either (R)-2-hydroxy-4-phenylbutyric acid or (S)-2-hydroxy-4-phenylbutyric acid, and the (R)-2-hydroxy-4-phenylbutyric acid or (S)-2-hydroxy-4-phenylbutyric acid thus produced is recovered to thereby give optically active 2-hydroxy-4-phenylbutyric acid. The optically active 2-hydroxy-4-phenylbutyric acid is an important intermediate in the synthesis of various drugs such as a remedy for hypertension.

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Niigata, Japan

Teruyuki Nikaido