Abstract: The present invention is to provide a process for efficiently producing an optically active alcohol including (R)-3-hydroxy-3-phenylpropanenitrile. One of the features of the present invention is a polypeptide having an activity of asymmetrically reducing 3-oxo-3-phenylpropanenitrile isolated from a microorganism belonging to the genus Candida to produce (R)-3-hydroxy-3-phenylpropanenitrile, DNA encoding the polypeptide and a transformant of producing the polypeptide. Another feature of the present invention is a process for producing an optically active alcohol such as (R)-3-hydroxy-3-phenylpropanenitrile by reducing a carbonyl compound such as 3-oxo-3-phenylpropanenitrile by use of the polypeptide or the transformant.

Abstract: The present invention has its object to provide a novel (S,S)-butanediol dehydrogenase. The present invention also has its object to provide a gene coding for the enzyme protein, a vector containing the gene, a transformant harboring the vector, and a method of producing an optically active alcohol using the transformant. The polypeptide according to one embodiment of the present invention has the physicochemical properties including actions such as: acting on (2S,3S)-2,3-butanediol to form (S)-acetoin in the presence of NAD+ as a coenzyme; and reducing 2,3-butanedione to form (2S,3S)-2,3-butanediol in the presence of NADH as a coenzyme.

Abstract: An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

Abstract: An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

Abstract: The present invention is to provide a process for simply producing an optically active 3-hydroxypropionic ester derivative useful as a medicament intermediate from an inexpensive material. More specifically, the present invention is directed to a process for producing an optically active 3-hydroxypropionic ester derivative comprising reacting an acetic ester derivative available at low cost with a base and a formic ester, thereby converting the acetic ester derivative into a 2-formylacetic ester derivative, and thereafter, stereospecifically reducing the formyl group of the derivative by use of an enzymatic source capable of stereoselectively reducing the formyl group of the derivative.

Abstract: A 2-formylacetic ester derivative represented by the general formula (5) is provided: where R4 represents an alkyl group having 2 to 6 carbon atoms; R5 represents an alkyl group having 1 to 10 carbon atoms; and X represents H, Li, Na or K.

Abstract: The present invention is to provide a process for efficiently producing an optically active alcohol including (R)-3-hydroxy-3-phenylpropanenitrile. One of the features of the present invention is a polypeptide having an activity of asymmetrically reducing 3-oxo-3-phenylpropanenitrile isolated from a microorganism belonging to the genus Candida to produce (R)-3-hydroxy-3-phenylpropanenitrile, DNA encoding the polypeptide and a transformant of producing the polypeptide. Another feature of the present invention is a process for producing an optically active alcohol such as (R)-3-hydroxy-3-phenylpropanenitrile by reducing a carbonyl compound such as 3-oxo-3-phenylpropanenitrile by use of the polypeptide or the transformant.

Abstract: The present invention provides a polypeptide having physicochemical characteristics of (1) to (5) described below: (1) action: to generate (S)-3-chloro-1,2-propanediol by stereoselectively reducing 1-chloro-3-hydroxyacetone using NADH as a coenzyme; (2) molecular weight: about 340,000 by gel-filtration and about 43,000 by SDS polyacrylamide gel electrophoresis; (3) optimum temperature: from 60 to 70° C.; (4) optimum pH for reduction: 6.0; and (5) optimum pH for oxidation: 9.0. Furthermore, the present invention provides a polypeptide comprising the amino acid sequence represented by SEQ ID NO: 1 in the Sequence Listing, a DNA encoding the polypeptide, and a transformant producing the polypeptide in large quantities. Still furthermore, the present invention provides a manufacturing method by using the above polypeptide or the above transformant of (S)-3-chloro-1,2-propanediol that is a useful material for pharmaceuticals, etc.

Abstract: The present invention provides a method enabling convenient production of an optically active secondary alcohol useful as a pharmaceutical intermediate, particularly an optically active 1,2-diol and an optically active 2-alkanol, from an enantiomer mixture thereof. An oxidizing enzyme source having the capability of selectively oxidizing one enantiomer of secondary alcohol is allowed to act on an enantiomer mixture of secondary alcohol in the presence of a reducing enzyme source having the capability of reverse enantio-selectively reducing a ketone derivative, to convert the enantiomer mixture into a substantially single enantiomer at a theoretical percent recovery of 100%, whereby an optically active secondary alcohol is produced.

Abstract: The present invention is to provide a process for simply producing an optically active 3-hydroxypropionic ester derivative useful as a medicament intermediate from an inexpensive material. More specifically, the present invention is directed to a process for producing an optically active 3-hydroxypropionic ester derivative comprising reacting an acetic ester derivative available at low cost with abase and a formic ester, thereby converting the acetic ester derivative into a 2-formylacetic ester derivative, and thereafter, stereospecifically reducing the formyl group of the derivative by use of an enzymatic source capable of stereoselectively reducing the formyl group of the derivative.