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Method for preparing methyl (S)-(+)-mandelate by microbial transformation of methyl benzoylformate

A technology of benzoylformic acid and methyl mandelic acid, applied in microorganism-based methods, biochemical equipment and methods, microorganisms, etc., can solve problems such as the decline of biotransformation efficiency, and achieve easy large-scale industrial production and mild reaction conditions. , the effect of increasing conversion volume

Active Publication Date: 2012-10-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The most traditional reaction system is the aqueous phase system, in which the catalytic activity of biotransformation microorganisms is high, but the biotransformation efficiency will drop sharply when the concentration of the organic substrate is too high

Method used

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  • Method for preparing methyl (S)-(+)-mandelate by microbial transformation of methyl benzoylformate
  • Method for preparing methyl (S)-(+)-mandelate by microbial transformation of methyl benzoylformate
  • Method for preparing methyl (S)-(+)-mandelate by microbial transformation of methyl benzoylformate

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Slant culture: Inoculate CGMCC No.2230 strains on the slant medium and culture at 30°C for 4-6 days. Slant medium composition: wort juice 10g / L, yeast powder 3g / L, peptone 5g / L, glucose 10g / L, agar 20g / L, natural pH value, solvent is water, sterilized at 121°C for 20min, cooled after sterilization Make a bevel.

[0032] Seed cultivation and fermentation: Both the seed and fermentation medium use liquid medium, the composition is glucose 30g / L, yeast powder 3g / L, ammonium sulfate 5g / L, anhydrous MgSO 4 0.25g / L, K 2 HPO 4 ·3H 2 O1g / L, KH 2 PO 4 1g / L, natural pH value, solvent is water. Use an inoculation needle to take a ring of bacteria from the slant medium and inoculate it into a 250ml Erlenmeyer flask containing 100ml of liquid medium, and culture it at 30°C and 180r / min for 24 hours to obtain a seed solution. Inoculate the seed solution with a 10% inoculum amount into a 250ml Erlenmeyer flask containing 100ml of liquid medium, culture it at 30°C and 180r / min f...

Embodiment 2

[0038] CGMCC No.2230 was cultivated according to the method in Example 1 to obtain bacterial cell fermentation broth. Mix 4 bottles of 100ml fermentation broth with a dry weight of 450mg bacteria with an equal volume of 2% sodium alginate solution to make a mixed solution, put the mixed solution into a syringe, and drop 3.5% CaCl 2 Form immobilized particles in the solution (1000ml), the diameter of the formed immobilized particles is 2mm, and solidify at 37°C for 30min, and the obtained immobilized particles are washed with sterile physiological saline to wash away excess calcium ions and uncaptured cells. The obtained 4 bottles of immobilized cell pellets continued to proliferate and culture in the fermentation medium for 0h, 24h, 48h and 72h respectively.

[0039] Add the 4 kinds of immobilized cell particles that have been proliferated and cultured into 300ml dibutyl phthalate containing 36.6mmol methyl benzoylformate, and carry out biotransformation under the conditions o...

Embodiment 3

[0043] CGMCC No.2230 was cultivated according to the method in Example 1 to obtain bacterial cell fermentation broth. Mix 4 bottles of 100ml fermentation broth with a dry weight of 450mg and an equal volume of 2% sodium alginate solution to make a mixture, put the mixture into syringes with different needle sizes, and drop 3.5% CaCl 2 (1000ml) to form immobilized particles in the solution, the diameters of the formed immobilized particles were 2mm, 3mm, 4mm and 5mm, and solidified at 37°C for 30min, and the obtained immobilized particles were washed with sterile normal saline to remove excess calcium ions and uncaptured cells, and the obtained immobilized cell particles continued to proliferate and culture in the fermentation medium for 72 hours.

[0044] Add the 4 kinds of immobilized cell particles that have been proliferated and cultured into 300ml dibutyl phthalate containing 36.6mmol methyl benzoylformate, and carry out biotransformation under the conditions of 30°C and ...

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Abstract

The invention provides a method for preparing methyl (S)-(+)-mandelate by the microbial transformation of methyl benzoylformate. The method comprises the following steps of: performing transformation reaction at the temperature of 20 to 35 DEG C for 8 to 96 hours in dibutyl phthalate by taking methyl benzoylformate as a substrate, and enzyme-containing thallus cells obtained by fermenting a Saccharomyces cerevisiae strain CGMCC No.2230 as a biocatalyst, and separating and purifying a transformation solution to obtain a product, namely the methyl (S)-(+)-mandelate. Reaction conditions are mild, the microbial transformation method is environment-friendly and is suitable for industrialized production, the product has high optical purity, the substrate is high in transformation rate, the separation and purification process is simple, and the catalyst can be recycled.

Description

(1) Technical field [0001] The invention relates to a method for preparing (S)-(+)-mandelic acid methyl ester by using Saccharomyces cerevisiae CGMCC No.2230 to asymmetrically reduce methyl benzoylformate. (2) Background technology [0002] (S)-(+)-Methyl(S)-(+)-mandelate, CAS accession number: 21210-43-5, molecular formula C 9 h 10 o 3 , molecular weight 166.1739. It is an important chiral drug intermediate, which can be widely used in the synthesis of chiral acids, chiral alcohols, chiral amine compounds, chiral amino alcohols and chiral thiols. The chiral compound prepared from (S)-(+)-methyl mandelate can be widely used in the preparation of chiral drugs. For example, (S)-(+)-mandelic acid prepared after hydrolysis of (S)-(+)-methyl mandelate can be used in the pharmaceutical industry for cefadroxazole, vasodilator cyclomandelate, eye drops hydroxy Intermediates such as benzazole, etc., can also be used as preservatives. [0003] (S)-(+)-methyl mandelate can be syn...

Claims

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Application Information

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IPC IPC(8): C12P7/62C12N11/10C12N11/04C12R1/865
CPCY02P20/50Y02P20/584
Inventor 欧志敏南颖康严琴英李仁玮
Owner ZHEJIANG UNIV OF TECH
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