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Method for preparing acyl-L-carnitine and/or L-carnitine

A technology of carnitine and acyl group, which is applied in the field of preparing acyl-L-carnitine and/or L-carnitine, and can solve the problems of low conversion rate of precursors, production stoppage, influence on market competitiveness, etc.

Inactive Publication Date: 2013-06-12
INST OF AGRO FOOD SCI & TECH CHINESE ACADEMY OF AGRI SCI
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Problems solved by technology

But take croton betaine as precursor to prepare the following problems in the method for L-carnitine: (1) precursor conversion rate is low
However, the transformation rate only reaches 42% of wild bacteria (Cánovas M, Bernal V, González M. Factors affecting the biotransformation of trimethylammonium compounds into 1-carnitine by Escherichia coli[J]. Biochemical Engineering Journal, 2005, 26: 145-154. ) and recombinant bacteria with a transformation rate of 70% (Castellar MR, Obón JM, Marín A.L(-)-carnitine production using a recombinant Escherichia coli strain[J]. Enzyme and Microbial Technology, 2001, 28: 785-791.), seriously affecting Its market competitiveness has been compromised, and related domestic enterprises have been forced to suspend production
(2) The product and precursor are difficult to separate
Sun Zhihao et al. (Sun Zhihao. Biocatalysis Technology [M]. Beijing: Chemical Industry Press, 2005: 503-532.) adopted the method of addition reaction of sulfite and croton betaine to realize the synthesis of croton betaine and L-carnitine Separation of alkali, but there is a problem that croton betaine cannot be recycled
In addition, from the perspective of the development of my country's carnitine industry, there is still a problem that there are fewer types of acyl-L-carnitine products

Method used

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  • Method for preparing acyl-L-carnitine and/or L-carnitine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1, preparation palmitoyl-L-carnitine

[0033] 1) Mix 20ml of [Bmim]PF 6 Ionic liquid (purchased from Henan Lihua Pharmaceutical Co., Ltd.), 1.5mmol croton betaine (Fan Liqiang, Yuan Qinsheng. Microbial conversion method-a new idea of ​​DL-carnitine untwisting [J]. Medicinal Chemistry, 1999, 34 (5): 335-337), 100mg KNO 3 , 200 mg of carnitine dehydratase and 1 ml of pH6.5 phosphate buffer solution were placed in a 125 ml round bottom flask, and reacted for 3 hours at 40° C. and 120 rpm on a vacuum rotary evaporator to obtain L-carnitine.

[0034] The reaction at this stage is the hydration reaction of L-carnitine from croton betaine catalyzed by carnitine dehydratase.

[0035] 2) Centrifuge the reaction solution of the above step 1) at 4200rpm for 1min to remove the carnitine dehydratase in the reaction system, place the separated carnitine dehydratase in 1ml of pH 6.5 phosphate buffer solution for the hydration reaction of the next cycle ; Then keep the re...

Embodiment 2

[0043] Embodiment 2, preparation palmitoyl-L-carnitine (the process of step 2-4 is not repeated)

[0044] 1) Mix 20ml of [Bmim]PF 6 Ionic liquid (purchased from Henan Lihua Pharmaceutical Co., Ltd.), 1.5mmol croton betaine (Fan Liqiang, Yuan Qinsheng. Microbial conversion method-a new idea of ​​DL-carnitine untwisting [J]. Medicinal Chemistry, 1999, 34 (5): 335-337), 100mg KNO 3 , 200mg of carnitine dehydratase and 1ml of pH6.5 phosphate buffer solution were placed in a 125ml round bottom flask, and reacted for 12h on a vacuum rotary evaporator at 30°C and 120rpm to obtain L-carnitine.

[0045] The reaction at this stage is the hydration reaction of L-carnitine from croton betaine catalyzed by carnitine dehydratase.

[0046] 2) Centrifuge the reaction solution in the above step 1) at 500rpm for 30min to remove the carnitine dehydratase in the reaction system, place the separated carnitine dehydratase in 1ml of pH 6.5 phosphate buffer solution for the hydration reaction of the ...

Embodiment 3

[0052] Embodiment 3, preparation of palmitoyl-L-carnitine (the process of steps 2-4 is repeated once)

[0053] 1) Mix 20ml of [Bmim]PF 6 Ionic liquid (purchased from Henan Lihua Pharmaceutical Co., Ltd.), 1.5mmol croton betaine (Fan Liqiang, Yuan Qinsheng. Microbial conversion method-a new idea of ​​DL-carnitine untwisting [J]. Medicinal Chemistry, 1999, 34 (5): 335-337), 50mg fumaric acid, 200mg carnitine dehydratase and 1ml pH6.5 phosphate buffer solution were placed in a 125ml round bottom flask, and reacted for 2h at 45°C and 120rpm on a vacuum rotary evaporator to obtain L- carnitine.

[0054] The reaction at this stage is the hydration reaction of L-carnitine from croton betaine catalyzed by carnitine dehydratase.

[0055] 2) Centrifuge the reaction solution of the above step 1) at 10000rpm for 0.5min to remove the carnitine dehydratase in the reaction system, place the separated carnitine dehydratase in 1ml of pH 6.5 phosphate buffer solution for the next cycle of hyd...

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Abstract

The invention discloses a method for preparing acyl-L-carnitine and / or L-carnitine, which comprises the following steps: 1) adding crotonbetaine and carnitine anhydrase to an aqueous solution containing [Bmim]PF6 ionic liquid, and reacting at 30-45 DEG C for 2-12h; 2) removing the carnitine anhydrase and water content in the reaction system in step 1); and 3) adding lipase and acyl donors to the reaction system in step 2), and reacting at 30-80 DEG C for 2-24h to obtain a reaction system containing the acyl-L-carnitine. The method for preparing acyl-L-carnitine has the following advantages: (1) the problem of low conversion rate in L-carnitine synthesis using crotonbetaine as a precursor is solved; (2) the problems on key technologies of product separation and purification in the L-carnitine synthesis using the crotonbetaine as the precursor are solved; and (3) the acyl-L-carnitine can be prepared. The acyl-L-carnitine can be used as the final product, and also can be hydrolyzed into L-carnitine.

Description

technical field [0001] The present invention relates to a method for preparing acyl-L-carnitine and / or L-carnitine. Background technique [0002] L-carnitine is widely used in pharmaceutical industry, food industry and feed industry. At present, the methods for producing L-carnitine mainly include extraction, chemical synthesis and biocatalysis. Among them, chemical synthesis and biocatalysis are of commercial value. Compared with the chemical synthesis method, the biocatalysis method has the characteristics of environmental friendliness, low cost, and high product safety, and has a better development prospect. [0003] The synthesis of L-carnitine from croton betaine under the catalysis of carnitine dehydratase is one of the important ways to prepare L-carnitine, and it is also the main method to produce L-carnitine by biocatalysis. However, the method for preparing L-carnitine with croton betaine as a precursor has the following problems: (1) The conversion rate of the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/00
Inventor 王强田金强张钟元
Owner INST OF AGRO FOOD SCI & TECH CHINESE ACADEMY OF AGRI SCI
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