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A method for splitting racemic leucine

A technology for spinning leucine and leucine, which is applied in the field of splitting racemic leucine, can solve the problems of being unsuitable for industrial production, increasing production costs, prolonging the production cycle, etc., and achieves convenient treatment and purification, easy hydrolysis, The effect of high equipment requirements

Inactive Publication Date: 2016-03-16
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The induced crystallization method to prepare D-leucine prolongs the production cycle and increases the production cost, and the optical purity of the product is relatively low, which is not suitable for industrial production

Method used

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  • A method for splitting racemic leucine

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Effect test

example 1

[0024] Weigh 3.62g (0.02mol) of leucine methyl ester hydrochloride into the small conical flask, then weigh 1.68g (0.02mol) of sodium bicarbonate into the conical flask, and measure 16ml of saturated lipase solution into the In the reaction flask, put the Erlenmeyer flask into a constant temperature oscillator to vibrate, set the reaction temperature to 38° C., react for 8 hours, then slowly cool down the reaction flask, and vacuum filter. Obtaining filter cake is L-leucine 1.02g, productive rate is 77.86%, specific rotation [α] D 20 =+14.6°(C=2, 6mol.L -1 HCl). The filtrate contains D-leucine methyl ester, add a certain amount of sodium hydroxide to the filtrate, add an equal volume of methanol after dissolving, stir at room temperature for 10h, and use 1mol.L -1 Adjust the pH of the solution to 6 with dilute hydrochloric acid, react for another 1 h, filter, wash the filter cake with water, and dry to obtain 0.90 g of D-leucine with a yield of 68.70%, [α] D 20 =-14.35°(C...

example 2

[0026] Take by weighing 3.62g leucine methyl ester hydrochloride and add in the small conical flask, then take by weighing 1.68g (0.02mol) sodium bicarbonate and add in the conical flask, and measure 16ml saturated lipase solution and add in the reaction flask, The Erlenmeyer flask was placed in a constant temperature oscillator to vibrate, the reaction temperature was 34° C., and the reaction time was 8 hours. Then, the reaction flask was cooled down slowly and vacuum filtered. Obtain filter cake and be L-leucine 0.92g, productive rate is 70.22%, specific rotation [α] D 20 =+14.6°(C=2, 6mol.L -1 HCl). The filtrate contains D-leucine methyl ester, add a certain amount of sodium hydroxide to the filtrate, add an equal volume of methanol after dissolving, stir at room temperature for 10h, and use 1mol.L -1 Adjust the pH of the solution to 6 with dilute hydrochloric acid, react for another 1 h, filter, wash the filter cake with water, and dry to obtain 0.94 g of D-leucine with...

example 3

[0028]Weigh 3.62g of leucine methyl ester hydrochloride and add it to the small conical flask, then weigh 1.68g of sodium bicarbonate and add it to the conical flask, and measure 16ml of saturated lipase solution and add it to the reaction flask. Put it into a constant temperature shaker to vibrate, set the reaction temperature to 38°C, react for 9 hours, then slowly cool down the reaction bottle, and vacuum filter. The obtained filter cake is L-leucine 1.19g, specific rotation [α] D 20 =+14.6°(C=2, 6mol.L -1 HCl). The filtrate contains D-leucine methyl ester, add solid sodium hydroxide to the filtrate, add methanol after dissolving, stir continuously for 10h, and use 1mol.L -1 Adjust the pH of the solution to 6 with dilute hydrochloric acid, react for another 1 h, filter, wash the filter cake with water, and dry to obtain 0.83 g of D-leucine with a yield of 63.36%, [α] D 20 =-14.40°(C=2, 6mol.L -1 HCl).

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Abstract

The invention relates to a method for splitting racemic leucine, which is characterized in that an enzyme method is used for splitting racemic leucine namely DL-leucine to prepare levorgyration leucine and dextrorotation leucine. The method comprises the following steps: 1)taking racemic leucine as a raw material, preparing the DL which is D-Leucine methyl ester hydrochloride according to a thionyl chloride method 2)dissolving D-Leucine methyl ester hydrochloride in an alkaline aqueous solution, adding lipase, performing enzymatic hydrolysis for 5-10 hours under 30-40 DEG C, gradually cooling to room temperature, filtering an insoluble substance to obtain levorgyration leucine which is L-leucine, and keeping a filtrate; and 3)continuously hydrolyzing the filtrate obtained in the step 2) under alkaline condition, neutralizing by using dilute acid after hydrolysis is completed, and filtering to obtain dextrorotation leucine which is D-leucine. A solvent used for splitting is water, the production cost is low, environmental pollution is less, the preparation technology is simple, purification is convenient, and equipment requirement is low.

Description

technical field [0001] The invention is a preparation technology of chiral organic compounds, especially a method for splitting racemic leucine. Background technique [0002] In terms of nutrition, L-leucine is an essential amino acid for the human body. L-leucine can be used as a nutritional supplement, such as in the preparation of amino acid infusions and comprehensive amino acid preparations. It works together with other amino acids to repair muscles, control blood sugar, and supply energy to body tissues. Research suggests that leucine can affect mechanisms that control energy balance in the body [1] ; Leucine has a significant effect on human fatigue resistance and control of muscle and liver glycogen degradation [2] ; Improve the body's oxidative capacity by completing the oxidation of carbohydrates and increase the density of mitochondria in skeletal muscle cells [3] . In addition, leucine can also be used in flavoring and flavoring agents. D-leucine is a non-na...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P41/00C12P13/06
Inventor 蒋立建付倩倩何慧唐赛杰顾美萍
Owner SOUTHEAST UNIV
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