Method for synthesizing D-arylglycine by using heterogeneous enzyme to catalytically hydrolyzing 5-arylhydantoin

A technology for catalytic hydrolysis of arylglycine, applied in the field of heterogeneous enzyme catalyzed hydrolysis of 5-arylhydantoin to synthesize D-arylglycine, can solve the problems of low solubility, large reaction volume, high energy consumption, etc. clip effect

Active Publication Date: 2008-01-16
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
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Problems solved by technology

[0003] The traditional preparation method of D-arylglycine includes chemical synthesis and resolution method and biocatalytic D-arylhydantoin hydrolysis method, wherein all reported technologies are liquid-liquid homogeneous processes, while homogeneous biocatalysis Synthesis of D-arylglycine by hydrolysis method leads to large reaction volume, low production capacity and high energy consumption due to its low solubility

Method used

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  • Method for synthesizing D-arylglycine by using heterogeneous enzyme to catalytically hydrolyzing 5-arylhydantoin

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Embodiment 1, the preparation of D-phenylglycine

[0060] In a 10L enzyme-catalyzed reaction tank, first add 7kg of water, then add 1kg of 5-phenylhydantoin, add hydrochloric acid or sulfuric acid to adjust the pH to 6.8, and then add wet enzyme activity of 0.62U / ml under stirring conditions The preparation solution is about 0.3L, the temperature is controlled at 28°C, and the reaction is stirred. Samples were taken at intervals of 6 hours, and the reaction was detected by liquid chromatography. When the reaction lasted for about 8 hours, D-phenylglycine crystals began to precipitate, and the product concentration in the reaction solution was basically constant at 2.45%. When the substrate 5-phenylhydantoin cannot be detected in the reaction system and the N-carbamoylglycine is below 0.25%, the reaction is basically completed, and the conversion rate is above 99.6%. The crude crystals obtained by sieving and separation can be recrystallized to obtain 446.2g of qualifie...

Embodiment 2

[0066] Embodiment 2, preparation of D-3-pyridine glycine

[0067] In a 10L enzyme-catalyzed reaction tank, first add 6.5kg of water, add 1kg of 5-(3-pyridyl)hydantoin under stirring conditions, adjust the pH to 6.5, and then add wet enzyme activity of 0.58U / ml Enzyme preparation solution is about 0.4L, stirred and reacted at 32-36°C. Samples were taken at intervals of 8 hours, and the reaction was detected by liquid chromatography. When the reaction lasted for about 9 hours, D-pyridine glycine crystals began to precipitate. When the substrate 5-(3-pyridyl)hydantoin cannot be detected in the reaction system and the N-carbamoylpyridine glycine is below 0.20%, the reaction is basically completed, and the conversion rate is about 99.5%. The coarse crystals obtained by sieving and separation can be recrystallized to obtain 391.6 g of qualified product D-3-pyridine glycine; the material that has passed through the sieve is obtained by membrane filtration, concentration and other re...

Embodiment 3

[0069] Embodiment 3, the preparation of D-2-naphthylglycine

[0070] In a 10L enzyme-catalyzed reaction tank, first add 7.5kg of water, add 0.8kg of 5-(2-naphthyl)hydantoin under stirring conditions, adjust the pH to 7.0, and then add wet enzyme activity to 0.65U / ml The enzyme preparation solution is about 0.4L, and the reaction is stirred at 30-40°C. Samples were taken at intervals of 8 hours, and the reaction was detected by liquid chromatography. When the reaction was carried out to about 7 hours, D-2-naphthylglycine crystals began to precipitate. When no 5-(2-naphthyl)hydantoin and corresponding intermediates can be detected in the reaction system, the reaction is basically finished, and the conversion rate is about 99%. The coarse crystals obtained by sieving and separation can be recrystallized to obtain 327.3g of qualified product D-2-naphthylglycine; the material that has passed through the sieve is obtained by membrane filtration, concentration and other refining pro...

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Abstract

The invention relates to a chemical pharmaceutical field, in particular to an approach on synthesis of D-aryl glycine by heterogeneous enzyme catalytic hydrolysis of 5-aryl hydantoin. The invention takes an enzyme preparation fermented by a mutant bacteria UV-LZ98 of a hydantoin producing strain Arthrobacter aurescens LZ-98 and a mutant bacteria UV-LZ99 of an ammonia methyl amidohydrolase producing strain Agrobacterium radiobacter LZ99 as a catalyst, and has a heterogeneous catalytic reaction with an input of more than three to ten times of 5-aryl hydantoin than homogeneous reaction to make the D-aryl glycine produced precipitate directly in a solid way during the substrate hydrolysis process, which improves the synthesis efficiency and lowers the evaporation energy consumption with a stable quality.

Description

technical field [0001] The invention relates to the field of chemical industry and pharmacy, in particular to a method for synthesizing D-arylglycine by hydrolyzing 5-arylhydantoin with heterogeneous enzyme catalysis. Background technique [0002] D-arylglycine is a very important class of non-natural amino acids. Because its configuration is just opposite to that of natural amino acids, it is mainly used in the synthesis and preparation of drugs, peptides and sweeteners. In recent years, with the increase in its application value Further development, the market demand is growing rapidly. [0003] The traditional preparation method of D-arylglycine includes chemical synthesis and resolution method and biocatalytic D-arylhydantoin hydrolysis method, wherein all reported technologies are liquid-liquid homogeneous processes, while homogeneous biocatalysis Due to the low solubility of D-arylglycine by hydrolysis, the reaction volume is large, the production capacity is low, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/04C12P39/00C12R1/06C12R1/01
CPCY02P20/10Y02P20/50
Inventor 刘守信甄小丽田霞李振朝李军章周志辉丁文科
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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