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Preparation method of (S)-(+)-ethyl mandelate by microbial transformed ethyl benzoylformate

A technology for ethyl benzoylformate and ethyl mandelic acid is applied in the field of microbial transformation of ethyl benzoylformate to prepare (S)-(+)-ethyl mandelic acid, and can solve problems such as decreased biotransformation efficiency, To achieve the effect of easy large-scale industrial production, cost saving and mild reaction conditions

Inactive Publication Date: 2012-10-10
杭州联豪科技有限公司
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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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  • Preparation method of (S)-(+)-ethyl mandelate by microbial transformed ethyl benzoylformate
  • Preparation method of (S)-(+)-ethyl mandelate by microbial transformed ethyl benzoylformate
  • Preparation method of (S)-(+)-ethyl mandelate by microbial transformed ethyl benzoylformate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Slant culture: Inoculate CGMCC No.2266 bacteria into the slant medium and culture at 30°C for 4-6 days. The composition of the slant medium is as follows: wort juice 10g / L, yeast powder 3g / L, peptone 5g / L, glucose 10g / L, agar 20g / L, natural pH, solvent is water, sterilized at 121°C for 20min, sterilized After cooling, make a slope.

[0031] Seed culture 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 O 1g / L, KH 2 PO 4 1g / L, natural pH value, solvent is water; sterilize at 121°C for 20 minutes, cool down after sterilization. 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% inoculation amount into a 2...

Embodiment 2

[0037] CGMCC No.2266 was cultivated according to the method in Example 1 to obtain bacterial cell fermentation broth. Mix 100ml of fermentation broth with a dry weight of 430mg of bacteria and 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 immobilized cell particles continued to proliferate and culture in the fermentation medium for 72 hours.

[0038] Add the cultured immobilized cell particles to 5 bottles of 300ml reaction system containing 2.2mmol, 4.4mmol, 5.5mmol, 7.7mmol and 10mmol of ethyl benzoylformate in water and n-hexane with a volume ratio of 1:1 , 30°C, 180r / min under the conditions of bio...

Embodiment 3

[0042] CGMCC No.2266 was cultivated according to the method in Example 1 to obtain bacterial cell fermentation broth. Mix 4 bottles of fermented broth with a dry weight of 430 mg of 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 (1000ml) solution to form immobilized particles, the diameter of the formed immobilized particles is 2mm, solidified at 37°C for 30min, the obtained immobilized particles were washed with sterile physiological saline to remove excess calcium ions and uncaptured cells, and the The obtained 4 bottles of immobilized cell pellets continued to proliferate and culture in the fermentation medium for 0h, 24h, 48h and 72h respectively.

[0043] The four kinds of immobilized cell granules that had been proliferated and cultured were respectively added to a 300ml reaction system containing 5.5mmol of ethyl benzoylformate, water and n-hexane with a volume ratio of 1...

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Abstract

The invention provides a preparation method of (S)-(+)-ethyl mandelate by using biocatalytic ethyl benzoylformate and taking saccharomyces cerevisiae with CGMCC No.2266 as a biocatalyst. The method comprises the following steps of: performing a conversion reaction for 8 to 120 hours at a temperature of between 20 and 35 DEG C in a water and n-hexane two-phase system by using ethyl benzoylformate as a substrate and the saccharomyces cerevisiae with CGMCC No.2266 as a biocatalyst; and separating and purifying the conversion solution to obtain (S)-(+)-ethyl mandelate. The microbial conversion method has the advantages of mild reaction condition, friendly environment, high product optical purity, high substrate conversion rate, simple separation and purification process and recyclable catalyst, and is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a method for preparing (S)-(+)-mandelic acid ethyl ester by biocatalyzing ethyl benzoylformate by using Saccharomyces cerevisiae CGMCC No.2266 as a biocatalyst. (2) Background technology [0002] (S)-(+)-mandelate ethyl ester (Ethyl(S)-(+)-mandelate), CAS accession number: 13704-09-1, molecular formula C 10 h 12 o 3 , molecular weight 180.2. 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. (S)-(+)-mandelic acid prepared by hydrolysis of ethyl (S)-(+)-mandelic acid can be used in the pharmaceutical industry for cefadroxazole, vasodilator cyclomandelate, eye drops oxybenzazole And other intermediates can also be used as preservatives. [0003] (S)-(+)-Ethyl mandelate can be synthesized mainly by chemical method and biotransformation method. Under the action of chemical catalyst or biol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/62C12N11/10C12N11/04C12R1/865
CPCY02P20/50Y02P20/584
Inventor 欧志敏严琴英南颖康谢开宇
Owner 杭州联豪科技有限公司
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