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Method for preparing D-amino acid by biological catalysis

A technology of biocatalysis and amino acid, which is applied in the field of compound preparation, can solve the problems of various types of emissions, high price, complex process, etc., and achieve the effect of controlling enantiomeric purity, short route and simple steps

Inactive Publication Date: 2011-06-15
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The former uses an asymmetric catalyst, which is expensive and difficult to recycle, and there are steps such as protection and deprotection in the process; the latter includes the Heine method, hydrolytic enzyme resolution method, etc., but each method requires multi-step reactions, the process is complicated, and the route Disadvantages such as long length and many types of emissions

Method used

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  • Method for preparing D-amino acid by biological catalysis
  • Method for preparing D-amino acid by biological catalysis
  • Method for preparing D-amino acid by biological catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1D

[0019] The preparation of embodiment 1D-tryptophan and indole acetic acid

[0020] In a 500mL shake flask (in 28 flasks at the same time), culture yeast Rhodotorulagraminis (ATCC 20804) (Rhodotorula pasture), grow for 24 hours, centrifuge, pour out the supernatant, freeze, ultrasonically break the wall, and make a homogenate , put it back into the shaker flask, add the same amount of racemate D, 50 mg of L-tryptophan to each bottle; adjust the pH to 7.3, ventilate the air, seal it with ventilation, put it back in the temperature-controlled shaker, shake it circularly, and At 0 hour, 6 hours and 12 hours, one milliliter sample was taken out for analysis in stages, followed by reaction progress, ultrafiltration, dilution, injected into HPLC for follow-up analysis, using Daiselu crown ether column, Crownpak CR(+), D-Try, tr=22min, L-Try, tr=30min. The analysis time was extended to 120 minutes. See results figure 1 , showing the change process of the amount of each substance in ...

Embodiment 2

[0022] The preparation of embodiment 2D-phenylalanine

[0023] In a 500mL shake flask, culture yeast Rhodotorula graminis (ATCC 20804) (Rhodotorula grass), grow for 24 hours, centrifuge, pour out the supernatant, freeze, ultrasonically break the wall, make a homogenate, divide evenly and shake back In the bottle, add the same amount of racemate D, L-phenylalanine 50 mg to each bottle; adjust the pH to 7.3, ventilate the air, put it back in the temperature-controlled shaker, shake it circularly, and take out one milliliter of samples for analysis in stages , track the reaction progress, in the reaction of 4h, 6h and 40h, ultrafiltration, dilution, injection into HPLC for tracking analysis, using Daise Crown Ether column, Crownpak CR (+), D-Phe, tr=7.5min, L-Phe , tr=11min. The analysis time was extended to 60 minutes. No other detectable products were found. Separation with ion exchange resin to obtain pure D-phenylalanine (D-Phe).

[0024] see figure 2 , is the change pro...

Embodiment 3D

[0026] The preparation of embodiment 3D-tyrosine

[0027] In a 500mL shake flask, culture yeast (Rhodotorula graminis) (ATCC 20804), grow for 24 hours, centrifuge, pour out the clear liquid, freeze, ultrasonically break the wall, make a homogenate, put it back into the shake flask, Add racemate D, 50 mg of L-tyrosine; adjust the pH to 7.3, ventilate the air, put it back in the temperature-controlled shaker, shake it in a circular manner, take out one milliliter of samples for analysis in stages, and track the reaction progress. After 4 hours of reaction , 6h and 40h, ultrafiltration, dilution, injected into HPLC for follow-up analysis, using a large road crown ether chromatographic column, Crownpak CR (+), D-Tyr, tr=6min, L-Tyr, tr=9min. The analysis time is extended to 60 minutes. Separation with ion exchange resin to obtain pure D-tyrosine (D-Tyr).

[0028] see image 3 , is the change process of the amount of each substance in the biotransformation process of tyrosine. ...

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Abstract

The present invention provides a biocatalysis preparation method of D-amino acid. Yeast (ATCC 20804) is centrifuged after being cultivated, and the clear liquid is poured out to be frozen, ultrasonic wall broken and homogenated, then the L-type in the racemate amino acid can be selectively oxidized to keep back the target product of D-type amino acid. The present invention can also use the livingcell as activator; when using the living cell, the freezing and the ultrasonic wall breaking are not required. The method provided by the present invention can be used to the preparation of D-type amino acid, and can be used to the elimination of L-adulterant in the D-type amino acid, and also can be used to the preparation of other D-type nonprotein amino acid. The method of the present invention needs not to adopt the commonly used steps of protection and protection again in the traditional method, and no metal catalyst and no organic solvent as well as additive are required in the preparation process, except the biomass, no chemical discharging exists, thus being a green environmental protecting production method. The present invention has the advantages that the design is reasonable, the preparation route is short, the step is simple, and the efficiency is high.

Description

technical field [0001] The invention belongs to a compound preparation method, relates to a biocatalytic preparation method of D-amino acid, mainly relates to a biocatalytic preparation method of D-tryptophan, D-phenylalanine, and D-tyrosine. Background technique [0002] Non-protein amino acids, such as D-amino acids and amino acid derivatives with different substituents, are important tools and basic raw materials for the development of modern new drugs. Non-protein amino acids with diverse structures have always been expensive in the world market, and the supply is in short supply. The ability to prepare non-protein amino acids is also a symbolic indicator of a country's new drug research and development capabilities. Compared with developed countries, my country lags far behind in this field. Due to the high added value of products and easy access to the market, the development of non-protein amino acid manufacturing technology is highly competitive. The current method...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/22C12P17/10C12R1/645
Inventor 张子张张晔斌
Owner ZHEJIANG UNIV
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