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Method for production of optically active alpha-hydroxycarboxylic acid

A manufacturing method and alkyl technology, applied in fermentation and other fields, can solve problems such as low selectivity, difficult separation, and complicated separation of α carbonyls and α hydroxyls

Inactive Publication Date: 2008-08-27
DAIICHI FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method has the disadvantage that the separation of α-carbonyls and α-hydroxyls is complicated, and sometimes the separation itself is difficult.
[0006] In addition, Japanese Patent Application Laid-Open No. 2-53497 and Japanese Patent Laid-Open No. 2-156892 are known as techniques related to the production of optically active substances characterized by enzymatic hydrolysis of α-aryl-α-hydroxy esters. However, the specific examples disclosed in these patent publications are limited to the method using mandelic acid, and there is a problem of low usefulness.
Also, Canadian Journal of Chemistry, 68(2), p.314, 1990 discloses a method for enzymatic hydrolysis of α-aryl-α-hydroxy acid esters having various substituents, but the enzymes used are limited to carbonic acid dehydration For enzymes, the optical purity of the product is only about 40 to 50% ee, and the selectivity is low, so there is a problem of low usefulness of this method

Method used

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  • Method for production of optically active alpha-hydroxycarboxylic acid
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  • Method for production of optically active alpha-hydroxycarboxylic acid

Examples

Experimental program
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Embodiment 1

[0058] A 5 mL culture medium containing 1% glucose, 0.5% peptone, and 0.3% yeast extract was used to shake culture Phyllanthus dermatitis NBRC 8193 for 6 days at 25°C. The bacteria are obtained by centrifugal separation or filtration. Add an appropriate amount of water, 50μL of 1M-MES buffer (pH 6.5), 10mg (50μL of 20% ethanol solution) racemic methyl 2-chlorophenylglycolate to the bacteria, and after mixing, take 1mL of the reaction solution , The reaction was shaken at 30°C for 20 hours. After the reaction, the reaction solution was centrifuged or filtered, and the supernatant was analyzed by HPLC (GL Sciences, Inertsil ODS-3, diameter 4.6mm, length 75mm, eluent: 25% acetonitrile, 75% 0.05M sodium phosphate buffer Liquid, pH 2.5, flow rate 1.0 mL / min, detection wavelength UV 254 nm). As a result, it was confirmed that 1.92 mg / mL of 2-chloromandelic acid was produced. In order to confirm the optical purity of the product, the sample was analyzed by HPLC (GEL PACKED COLUMN CRS10W,...

Embodiment 2

[0065] 5 mL of medium containing 1% glucose, 0.5% peptone, and 0.3% yeast extract was used to shake culture Rhizobium radiata NBRC 13263 for 6 days at 25°C. The bacteria are obtained by centrifugal separation or filtration. Add an appropriate amount of water, 50μL of 1M-MES buffer (pH 6.5), 10mg (50μL of 20% ethanol solution) racemic methyl 2-chlorophenylglycolate, after mixing, take 1mL of the reaction solution, The reaction was shaken at °C for 20 hours. After the reaction, the reaction solution was centrifuged or filtered, and the supernatant was analyzed by HPLC (GL Sciences, Inertsil ODS-3, diameter 4.6mm, length 75mm, eluent: 25% acetonitrile, 75% 0.05M sodium phosphate buffer Liquid, pH 2.5, flow rate 1.0 mL / min, detection wavelength UV 254 nm). As a result, it was confirmed that 1.71 mg / mL of 2-chloromandelic acid was produced. In order to confirm the optical purity of the product, the sample was analyzed by HPLC (GEL PACKED COLUMN CRS10W, manufactured by Mitsubishi Chemic...

Embodiment 3

[0071] 5 mL of medium containing 1% glucose, 0.5% peptone, and 0.3% yeast extract was used to shake culture Rhizobium radiata NBRC 13263 for 6 days at 25°C. The bacteria are obtained by centrifugal separation or filtration. Add an appropriate amount of water, 50μL of 1M-MES buffer (pH 6.5), 10mg (50μL of 20% ethanol solution) racemic methyl 2-chlorophenylglycolate, after mixing, take 1mL of the reaction solution, The reaction was shaken at °C for 72 hours. After the reaction, the reaction solution was centrifuged or filtered, and the supernatant was analyzed by HPLC (GL Sciences, Inertsil ODS-3, diameter 4.6mm, length 75mm, eluent: 25% acetonitrile, 75% 0.05M sodium phosphate buffer Liquid, pH 2.5, flow rate 1.0 mL / min, detection wavelength UV 254 nm). As a result, it was confirmed that 5.04 mg / mL of unreacted methyl 2-chloromandelate remained. In order to confirm the optical purity of the residue, the sample was analyzed by HPLC (manufactured by CHIRALCEL OJ DAICEL, diameter 4.6m...

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Abstract

Disclosed is a method for efficient production of an optically active alpha-hydroxycarboxylic acid represented by the general formula (I): (I) wherein A represents a residue of a 5- or 6-membered cyclic compound; * represents a carbon atom having an S- or R-configuration; and X represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. The method comprises the step of treating an ester compound (optically not pure) corresponding to the desired a-hydroxycarboxylic acid with a cell or culture of a microorganism belonging to the genus Leifsonia, Cylindrocarpon or Verticillium or a product produced by treating the cell or culture or an extract from the cell or culture.

Description

Technical field [0001] The present invention relates to a method for producing optically active α-hydroxy carboxylic acid or optically active α-hydroxy carboxylic acid ester. More specifically, the present invention relates to a method for efficiently producing optically active α-hydroxy carboxylic acid or optically active α-hydroxy carboxylic acid ester from a racemic mixture of α-hydroxy carboxylic acid ester using microorganisms. Background technique [0002] α-Hydroxycarboxylic acid or its derivatives are useful as intermediates for the manufacture of various medicines and pesticides, especially since the optically active α-hydroxycarboxylic acid or its ester derivatives having an asymmetric center at the α position can be used Various physiologically active compounds are produced, and therefore, methods for efficiently producing optically active α-hydroxycarboxylic acids or their ester derivatives with high optical purity have been intensively studied. For example, it is kno...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00
CPCC12P7/62C12P7/42C12P41/00C12P7/56
Inventor 坂本惠司北伸二森井亮博
Owner DAIICHI FINE CHEM CO LTD