Abstract: The present invention relates to a method for producing an optically active 3-aminopiperidine or salt thereof. In the method, a racemic nipecotamide is stereoselectively hydrolyzed to obtain an optically active nipecotamide and an optically active nipecotic acid in the presence of an enzyme source derived from an organism, and then the optically active nipecotamide is derived into an optically active aminopiperidine or salt thereof by aroylation, Hofmann rearrangement, deprotection of the amino group and further deprotection; or the optically active nipecotamide is derived into an optically active aminopiperidine or salt thereof by selective protection with BOC, Hofmann rearrangement and further deprotection. It is possible by the present invention to produce an optically active 3-aminopiperidine or salt thereof useful as a pharmaceutical intermediate from an inexpensive and easily available starting material by easy method applicable to industrial manufacturing.

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 relates to a process for producing an optically active 2-substituted propanal derivative, and more particularly, a process for producing an optically active 2-substituted propanal derivative which comprises stereoselectively reducing a carbon-carbon double bond of a 2-substituted acrolein derivative by using an enzyme source capable of stereoselectively reducing said carbon-carbon double bond. According to the present invention, it becomes possible to produce an optically active 2-substituted propanal derivative, in particular an optically active 2-alkylpropanal derivative, which is useful as an intermediate of pharmaceutical products, sweetening agents, etc., in a convenient manner from inexpensive and easily available materials.

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 relates to a process for producing an optically active 1,4-pentanediol by asymmetrically reducing 5-hydroxy-2-pentanone, which is easily available at low cost. The present invention also relates to a process for producing an optically active 1-substituted 2-methylpyrrolidine including sulfonylating the optically active 1,4-pentanediol to convert it to an optically active sulfonate compound, and reacting the compound with an amine. According to the processes of the present invention, an optically active 1,4-pentanediol and an optically active 1-substituted 2-methylpyrrolidine, which are useful as an intermediate for medicines and an intermediate for agricultural chemicals, can be simply produced from an inexpensive starting material.

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.

Abstract: The present invention provides a process for easily preparing a (S)-&agr;-halomethylpyridine-methanol derivative, which is useful as an intermediate of pharmaceutical products, from inexpensive raw materials. The (S)-&agr;-halomethylpyridine-methanol derivative is prepared by (S)-selectively reducing a 2-haloacetylpyridine derivative using an enzyme source having ability to (S)-selectively reduce a carbonyl group of the 2-haloacetylpyridine derivative, which can be obtained inexpensively. Also, a hydrohalic acid salt of (S)-&agr;-halomethyl-3-pyridine-methanol derivative is isolated and purified as crystal from a (S)-&agr;-halomethyl-3-pyridine-methanol derivative containing impurities using hydrohalic acid and an organic solvent.

Abstract: The present invention provides a method capable of simply producing optically active halopropanediol derivatives useful as pharmaceutical intermediates from inexpensive raw materials.

Abstract: The present invention has an object to provide a process for easily producing optically active N-aryl-1-amino-2-propanol derivatives which are of value as pharmaceutical intermediates from inexpensive starting materials.

Abstract: A process for efficiently preparing an optically active chloropropanediol derivative, especially (S)-1-benzyloxy-3-chloro-2-propanol, which has a high optical purity and is useful as an intermediate for medicines. The process comprises treating an inexpensive racemic chloropropanediol derivative with a nitroxyl compound and an oxidizing agent to convert it into a chlorohydroxyacetone derivative and then stereospecifically reducing the carbonyl group of the chlorohydroxyacetone derivative by the action of either a carbonyl-reducing enzyme having the ability to stereospecifically reduce the chlorohydroxyacetone derivative or an optically treated culture of a microorganism having the ability to yield the carbonyl-reducing enzyme. Thus, an optically active chloropropanediol derivative is prepared.

Abstract: It is an objective to produce intermediates of optically active beta-3 adrenaline receptor agonists from readily available raw materials in a safe, efficient and industrially advantageous manner.

Abstract: It is an objective to produce intermediates of optically active beta-3 adrenaline receptor agonists from readily available raw materials in a safe, efficient and industrially advantageous manner. A substituted acetylpyridine derivative represented by the general formula (9) is reduced by enantioselective reduction to produce an optically active hydroxyethylpyridine derivative represented by the general formula (10) (wherein * represents an asymmetric carbon atom), and it is further derivatized to an intermediate of an optically active beta-3 adrenaline receptor agonist, such as an optically active dihydroxyethylpyridine derivative represented by the general formula (14) or an optically active oxirane derivative represented by the general formula (16).

Abstract: It is an objective to produce intermediates of optically active beta-3 adrenaline receptor agonists from readily available raw materials in a safe, efficient and industrially advantageous manner. A substituted acetylpyridine derivative represented by the general formula (9) is reduced by enantioselective reduction to produce an optically active hydroxyethyl derivative represented by the general formula (10) (wherein * represents an asymmetric carbon atom), and it is further derivatized to an intermediate of an optically active beta-3 adrenaline receptor agonist, such as an optically active dihydroxyethylpyridine derivative represented by the general formula (14) or an optically active oxirane derivative represented by the general formula (16).

Abstract: A process for efficiently preparing an optically active chloropropanediol derivative, especially (S)-1-benzyloxy-3-chloro-2-propanol, which has a high optical purity and is useful as an intermediate for medicines. The process comprises treating an inexpensive racemic chloropropanediol derivative with a nitroxyl compound and an oxidizing agent to convert it into a chlorohydroxyacetone derivative and then stereospecifically reducing the carbonyl group of the chlorohydroxyacetone derivative by the action of either a carbonyl-reducing enzyme having the ability to stereospecifically reduce the chlorohydroxyacetone derivative or an optically treated culture of a microorganism having the ability to yield the carbonyl-reducing enzyme. Thus, an optically active chloropropanediol derivative is prepared.

Abstract: This invention provides an easy and efficient process for producing a simvastatin of great use as an HMG-CoA reductase inhibitor, which comprises deacylation of lovastatin with an inorganic base and a secondary or tertiary alcohol and subjecting the resulting diol lactone to selective protection with a ketal or acetal protective group, acylation and deprotection-lactonization to give simvastatin.

Abstract: The present invention has for its object to provide a method for producing an L-allysine acetal which involves a fewer steps and is efficient. This invention relates to method for producing an L-allysine acetal which comprises; converting a D,L-allysine acetal of the following general formula (1) (wherein R1 and R2 are the same or different, and each of them represents an alkyl group having 1 to 8 carbon atoms, or they combinedly form a ring and represent an alkylene group having 2 to 8 carbon atoms) to a mixture of a 2-oxo-6,6-dialkoxyhexanoic acid of the following general formula (2) (wherein R1 and R2 are as defined above) and an L-allysine acetal of the following general formula (3) (wherein R1 and R2 are as defined above) by reacting in the presence of an enzyme capable of stereoselective oxidative deamination of D-amino acids and; isolating said L-allysine acetal after said converting.