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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

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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 for preparing the unnatural amino acid 3-(2-thienyl)-L-alanine. Simple and easy to control, low cost, less solvent used, less pollution, suitable for large-scale production

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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Effect test

Embodiment 1

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

[0042] Concrete fermentation condition is: the bacterium that produces enzyme 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. Use sodium hydroxide solution to adjust the pH to 7.5-7.7, inoculum amount of seed solution is 5-10% (v / v), culture at 35-37°C for 20-24 hours at 160 rpm, microscopic examination is full, and OD value 0.4-0.6, enzyme activity: 0.5-0.6umol / (ml.min). The enzyme is an intracellular enzyme and does not need to break the wall. After fermentation, the fermentation broth containing bacteria can be used directly, or it can be used after centrifugation.

Embodiment 2

[0044] (1) Add 500ml of water into a 1000ml four-neck flask equipped with a stirring, ventilating and reflux device, then add 100g (1mol) hydantoin and 5g (0.08mol) ethanolamine, stir fully, protect with nitrogen, and keep warm in a water bath for 10 to 15 ℃, 106g (0.95mol) 2-thiophene formaldehyde was added dropwise, and the dropwise addition was completed in 2 hours. After the drop, the temperature was raised to 85°C, and the temperature was kept for 3 hours. It was detected that there was no 2-thiophene formaldehyde in the solution, and the temperature was continued to rise to 95°C. hour, cooled to room temperature, suction filtered, washed with a small amount of water, and dried to obtain 175.2 g of 2-thiophene hydantoin (yield 95.5%, purity 99.4%);

[0045] (2) Add 500ml of water to a 1000ml four-necked flask with stirring, ventilating and reflux devices, then add 50g (0.26mol) 2-thiophene hydantoin and 24g (0.6mol) sodium hydroxide, fully stir, and Under protection, heat...

Embodiment 3

[0049] (1) Add 500ml of water into a 1000ml four-neck flask with a stirring, ventilating and reflux device, then add 100g (1mol) hydantoin and 5.5g (0.073mol) n-propanolamine, stir well, pass nitrogen protection, and water bath Keep warm at 10-15°C, add 106g (0.95mol) 2-thiophene carboxaldehyde dropwise, and finish the dropwise addition in 2 hours, then raise the temperature to 85°C, keep warm for 3 hours, check that there is no 2-thiophene carboxaldehyde in the solution, continue to heat up to 95 ℃, keep warm for 1 hour, cool down to room temperature, filter with suction, wash with a small amount of water, and dry to obtain 171.2 g of 2-thiophene hydantoin (yield 92.7%, purity 99.2%);

[0050] (2) Add 500ml of water to a 1000ml four-necked flask with a stirring, ventilating and reflux device, then add 50g (0.26mol) 2-thiophene hydantoin and 30g (0.75mol) sodium hydroxide, fully stir, and Under protection, the temperature was raised to 90°C for heat preservation and hydrolysis...

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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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