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Process for producing optically active alcohol and carboxylic acid

An optically active and optically pure technology, applied in the field of preparation of optically active alcohols and carboxylic acids, can solve the problems of a large number of solvents, low efficiency, long time, etc.

Inactive Publication Date: 2007-04-18
API CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it takes a long time (12 hours or more) to react with malonate, and requires a large amount of solvent (50 times the volume) when recrystallizing with dicarboxylic acid, and high temperature (180°C) is required in the decarboxylation reaction, which is cost-effective Low, so there are many disadvantages in terms of industrial implementation
And for the optical purity of these compounds only the optical rotation is reported, the correct optical purity is still unclear

Method used

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  • Process for producing optically active alcohol and carboxylic acid
  • Process for producing optically active alcohol and carboxylic acid
  • Process for producing optically active alcohol and carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A

[0229] Embodiment A (use microorganism to prepare the alcohol with optical activity)

[0230] (1) Isolation of microorganisms that produce (S)-2-pentanol from 2-pentanone and microorganisms that produce (S)-2-hexanol from 2-hexanone

[0231] Liquid containing 5g / L yeast extract (manufactured by Difco), 5g / L polypeptone (manufactured by Nippon Pharma), 3g / L malt extract (manufactured by Difco), 20g / L glucose (manufactured by Nippon Food Processing) in 2.5mL Various bacterial strains shown in Table 1 were inoculated in the culture medium, and aerobically cultured at 30° C. for 24-72 hours. 1 mL of the culture solution was taken from each of the obtained culture solutions, and bacterial cells were collected by centrifugation. Add 0.04mL Tris-HCl buffer solution (pH 7.0) and 9.028mL desalted water to the cells to fully suspend the cells, then add 0.05mL 100g / L glucose, 9.02mL 12g / L NADP + (manufactured by Oriental Yeast), and 0.01 mL of the reaction substrate 2-pentanone or 2-he...

Embodiment B

[0301] Embodiment B (preparation of optically active carboxylic acid by chemical synthesis)

Embodiment 1

[0302] (Embodiment 1) Synthesis of (S)-2-methanesulfonyloxypentane

[0303] Into a 200 mL three-necked flask were added 4.14 g (47.0 mmol, 99.1% e.e.) of (S)-2-pentanol and 9.8 mL (71 mmol) of triethylamine, 41 mL of dichloromethane. The mixture was ice-cooled, and 4.36 mL (56.4 mmol) of methanesulfonyl chloride was added dropwise. After stirring for 30 minutes, 40 mL of saturated ammonium chloride aqueous solution and 20 mL of water were added to terminate the reaction. The mixture was extracted with 80 mL of diethyl ether, and the organic layer was washed with 20 mL of saturated aqueous ammonium chloride solution and 20 mL of saturated brine, and dried over magnesium sulfate. The solvent was distilled off to obtain 8.5 g of crude (S)-2-methanesulfonyloxypentane, which was used in the following reaction without further purification.

[0304] 1 H-NMR (400MHz, CDCl 3 )δ0.95(t, J=7.2Hz, 3H), 1.42(d, J=6.3Hz, 3H), 1.34-1.50(m, 2H), 1.50-1.63(m, 1H), 1.67-1.77(m , 1H), 3.00(s...

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Abstract

It is an object of the present invention to provide a low-cost and efficient industrial process for producing (S)-2-pentanol, (S)-2-hexanol, 1-methylalkylmalonic acid and 3-methylcarboxylic acid with high optical purity. There is provided a process for producing (S)-2-pentanol and (S)-2-hexanol, comprising causing a certain type of microbe or transformed cells, a treatment mixture from the microbe or cells, a culture solution of the microbe or cells and / or a product of crude purification or purification of a carbonyl reductase fraction obtained from the microbe or cells to act on 2-pentanone and 2-hexanone, respectively.

Description

technical field [0001] The present invention relates to the preparation of intermediate raw materials for medicines, pesticides, etc. The method for industrially useful compound (S)-2-pentanol or (S)-2-hexanol also involves making transformed cells expressing the following DNA, the cell treatment and / or the cell culture fluid with 2- A method for preparing (S)-2-pentanol or (S)-2-hexanol by the action of pentanone or 2-hexanone, wherein the DNA code is obtained from the above-mentioned microorganism, has a reduced carbonyl group and synthesizes an optically active alcohol Ability of protein (carbonyl reductase). The present invention also relates to optically active 1-methylalkylmalonic acid and its preparation method, and optically active 3-methylcarboxylic acid preparation method. Background technique [0002] Known methods for the chemical preparation of (S)-2-pentanol or (S)-2-hexanol are, for example, the reaction of 2- A method for reducing pentanone (J.Am.Chem.Soc....

Claims

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Application Information

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IPC IPC(8): C12N15/53C07C55/08C12P7/04C12P7/40C12P7/44
Inventor 出来岛康方川端润平冈宏敏上田诚上原久俊
Owner API CO LTD
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