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Preparation method of R-o-chloromandelic acid and alcohol ester thereof

A technology of o-chloromandelic acid and amino acid, applied in the field of bioengineering, can solve problems such as high cost and complicated production process, and achieve the effects of low cost, short reaction time and high yield

Inactive Publication Date: 2012-09-12
ZHENGZHOU TUOXIN INST OF BIOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the participation of the highly toxic substance HCN in the reaction, there is a great potential safety hazard and environmental pressure
Using a specific carbonyl reductase to reduce methyl o-chloroacetophenone, and then obtain a single R-methyl o-chloromandelate through separation and purification, but this method requires the addition of a specific cofactor NADP + (Nicotinamide adenine dinucleotide phosphate), so that the reaction continues in the direction of reduction, the cost is high, and the above method often needs to adjust the conversion reaction system, such as two-phase catalysis and ionic liquid reaction system, in order to obtain more High yield and optical purity, the production process is more complicated

Method used

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  • Preparation method of R-o-chloromandelic acid and alcohol ester thereof
  • Preparation method of R-o-chloromandelic acid and alcohol ester thereof
  • Preparation method of R-o-chloromandelic acid and alcohol ester thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Example 1: The preparation method of R-o-chloromandelic acid comprises the following steps:

[0037] (1) Recombinant expression of enzymes

[0038] Design primer pair P1, P2:

[0039] P1: 5'-atacgcggatccatgtggaacaatgctccgc3', P2: 5'-gggccgctcgagttaacttctcgcttgttc3',

[0040] Pseudomonas fluorescens ( Pseudomonas fluorescens ) genomic DNA as a PCR template for PCR amplification, the PCR system is: 10×Taq buffer 5μl; 10 mmol / L dNTP 1.5μl; 25 mmol / L MgCl 2 3μl; 1μl each of upstream and downstream primers; 1μl DNA template; 5U / μl Taq DNA polymerase 0.25μl; ddH 2 O 37.25μl; PCR amplification steps are: (1) 95°C, pre-denaturation for 3min; (2) 94°C, denaturation for 30s; (3) 50°C annealing for 30s; (4) 72°C extension for 75s; repeat step (2) ~(4) 30 times; (5) Continue to extend at 72°C for 10min, then cool to 4°C. The PCR product was purified by agarose gel electrophoresis, and the target band in the 1100-1200bp interval was recovered by using the agarose gel DNA rec...

Embodiment 2

[0052] Example 2: The preparation method of R-methyl o-chloromandelate is substantially the same as Example 1, comprising the following steps:

[0053] Esterify racemic o-chloromandelic acid with methanol under the action of concentrated sulfuric acid to produce racemic o-chloromandelic acid methyl ester. The following steps are the same as steps (1), (2), (3) and (4) in Example 1, and finally R-methyl o-chloromandelate is obtained.

[0054] The preparation of other alcohol esters only needs to change the esterified alcohol into the corresponding alcohol.

[0055]

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PUM

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Abstract

The invention discloses a preparation method of R-o-chloromandelic acid and alcohol ester thereof. The method comprises the step that through inductively expressing recombinant S-mandelate dehydrogenase, carbonyl reductase and glucose dehydrogenase, using racemic o-chloromandelic acid or the alcohol ester thereof and glucose as substrates and conducting a sequential catalytic reaction, the R-o-chloromandelic acid and the alcohol ester thereof are obtained. Adopted genetic engineering bacteria are escherichia coli, bacillus subtilis, aeruginosa and saccharomyces cerevisiae. The method is an environmentally-friendly and economic preparation method of a single optcial antimer of the R-o-chloromandelic acid, has the advantages of short reaction time, low energy consumption and high yield and is easy to operate; and the yield of the R-o-chloromandelic acid (or the alcohol ester thereof) is larger than 86 percent, and the enantiomeric excess (ee) value of the R-o-chloromandelic acid (or the alcohol ester thereof) is above 95 percent. By using the preparation method, the racemic o-chloromandelic acid which has a low price and is easy to obtain is biologically catalyzed to the R-o-chloromandelic with important industrial value, so that the preparation method requires a low cost, is green and environmentally friendly, needs a simplified process and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of bioengineering, and relates to o-chloromandelic acid and its alcohol esters, in particular to a preparation method of R-o-chloromandelic acid and its alcohol esters. Background technique [0002] O-chloromandelic acid or its alcohol ester is an important pharmaceutical and chemical intermediate. The preparation of single enantiomer R-o-chloromandelic acid and its alcohol esters relies on three types of methods: chemical methods, physical methods and biological methods. (1) Chemical method, mainly using chiral amine compounds to form diastereoisomeric salts to obtain single enantiomers, or asymmetric synthesis of o-chloroacetophenone methyl ester by using a certain reducing agent A single configuration of methyl mandelate. (2) Physical method, used for enantiomeric resolution of o-chloromandelic acid or its alcohol esters, such as chromatography, crystallization, membrane and supercritical extraction. R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P7/42C12P7/62C12N15/70C12R1/19
Inventor 王海勇吴阔
Owner ZHENGZHOU TUOXIN INST OF BIOLOGY
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