Method for preparing 3-(2-thienyl)-L-alanine

A technology of thiophenepyruvate and alanine, which is applied in the direction of fermentation, can solve the problems of low yield, high cost, and cumbersomeness, and achieve the effects of high yield, low production cost, and cost reduction

Active Publication Date: 2018-12-21
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the technical problems of cumbersomeness, high cost and low yield in the existing technology, and provide a method

Method used

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  • Method for preparing 3-(2-thienyl)-L-alanine
  • Method for preparing 3-(2-thienyl)-L-alanine
  • Method for preparing 3-(2-thienyl)-L-alanine

Examples

Experimental program
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Example Embodiment

[0040] Example 1

[0041] Preparation of fermentation broth containing L-aspartate aminotransferase:

[0042] The specific fermentation conditions are: the enzyme producing bacteria is Escherichia coli (Escherichiacolt, ATCC11303), 1.5% glucose, 0.6% peptone, 0.1% beef extract, 2% corn steep liquor, 0.05% sodium chloride, 0.05% magnesium sulfate, 0.05% sulfuric acid Ammonium. Adjust the pH to 7.5~7.7 with sodium hydroxide solution, the seed solution inoculum amount is 5~10% (v / v), culture at 35~37℃ for 20~24h under the condition of 160 revolutions / min, full microscopic examination, OD value It is 0.4-0.6, enzyme activity: 0.5-0.6umol / (ml.min). The enzyme is an intracellular enzyme and does not need to be broken. The fermentation broth containing bacteria can be used directly after fermentation, or it can be used after centrifugal preservation.

Example Embodiment

[0043] Example 2

[0044] (1) Add 500ml of water to a 1000ml four-necked flask equipped with stirring, aeration and reflux devices, then add 100g (1mol) hydantoin and 5g (0.08mol) ethanolamine, stir well, protect by nitrogen, and keep the water bath for 10-15 ℃, add 106g (0.95mol) 2-thiophenecarboxaldehyde dropwise, after 2 hours of dripping, the temperature is increased to 85°C after the completion of the dripping, and the temperature is kept for 3 hours. It is detected that there is no 2-thiophenecarboxaldehyde in the solution, and the temperature is continued to 95°C for 1 After hours, cooled to room temperature, filtered with suction, washed with a small amount of water, and dried to obtain 175.2g of 2-thienohydantoin (yield 95.5%, purity 99.4%);

[0045] (2) Add 500ml of water to a 1000ml four-necked flask equipped with stirring, aeration and reflux devices, and then add 50g (0.26mol) 2-thienyahydantoin and 24g (0.6mol) sodium hydroxide, stir thoroughly, Under protection, hea...

Example Embodiment

[0048] Example 3

[0049] (1) Put 500ml of water into a 1000ml four-necked flask equipped with stirring, aeration and refluxing devices, then add 100g (1mol) hydantoin and 5.5g (0.073mol) n-propanolamine, stir well, protect with nitrogen, and water bath Keep the temperature at 10~15℃, add 106g (0.95mol) 2-thiophene formaldehyde dropwise. After 2 hours, the dripping is completed. After the dripping, the temperature is raised to 85℃ and the temperature is kept for 3 hours. It is detected that there is no 2-thiophene formaldehyde in the solution, and the temperature is continued to 95 Incubate at ℃ for 1 hour, cool to room temperature, filter with suction, wash with a small amount of water, and dry to obtain 171.2g of 2-thiphenyhydantoin (yield 92.7%, purity 99.2%);

[0050] (2) Add 500ml of water to a 1000ml four-necked flask equipped with stirring, aeration and reflux devices, and then add 50g (0.26mol) 2-thienyahydantoin and 30g (0.75mol) sodium hydroxide, stir thoroughly, Under p...

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Abstract

The invention discloses a method for preparing 3-(2-thienyl)-L-alanine. The method comprises the following steps: (1) carrying out a condensation reaction on hydantoin and 2-thiophene formaldehyde under the protection of inert gas in the presence of a catalyst and water to obtain 2-thiophene hydantoin; (2) carrying out hydrolytic reaction on the 2-thienylidene under the protection of inert gas inthe presence of alkali and water to obtain a 2-thienylidene pyruvic acid reaction liquid; and (3) adding water and L-aspartic acid to the reaction liquid obtained in the step (2), and carrying out enzyme conversion reaction under the action of L-aspartic transaminase to obtain 3-(2-thienyl)-L-alanine. The method provided by the invention has the advantages of simple and convenient operation, safety, high efficiency, mild reaction condition, less pollution, high reaction yield and good product quality, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of polypeptide synthesis, and in particular relates to a method for preparing 3-(2-thienyl)-L-alanine. Background technique [0002] 3-(2-thienyl)-L-alanine is an important nitrogen and sulfur heterocyclic compound, and its derivatives have good anticancer, antimalarial, antibacterial, antioxidative and antiviral and other biological activities , is widely used in the research and development and screening of drug molecules. It belongs to heterocyclic unnatural amino acids. It is mainly used in the fields of peptide synthesis, medicine and chemical industry. It can be used as a common inhibitor of bacterial culture. In the study of tumor chemotherapy, the research has Antimetabolites of thienyl amino acids are a new research direction. [0003] In the current prior art, the preparation method route of unnatural amino acid 3-(2-thienyl)-L-alanine is 2 types: 1, chemical synthesis of 3-(2-thienyl)-L-alanine, 2-thiophe...

Claims

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Application Information

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IPC IPC(8): C12P17/00
CPCC12P17/00
Inventor 乔浩于荣华赵航宇刘存礼蔡家威
Owner NANJING UNIV OF TECH
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