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Method for simultaneously preparing D-tert-leucine and L-tert-leucine

A technology of tertiary leucine and aminolysis reaction, applied in the field of biocatalysis, can solve problems such as low solubility and unfavorable production, and achieve the effects of improving solubility, low cost and realizing biocatalysis

Inactive Publication Date: 2016-03-16
NANJING Y BIO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The patent "Production of L-tert-leucine by continuous enzymatic method" 201010622182 uses phenylacetyl to modify the helical tertiary-leucine, and uses immobilized Amanoacylase to split at room temperature. The enzyme relies on imports, and the phenylacetyl Modified tertiary leucine has low solubility at room temperature, and the process is unfavorable to production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Dissolve 1 liter (10.9 moles) of n-butanol in 2.3 liters of concentrated sulfuric acid, and slowly add 964ml (12 moles) of 1,1-dichloroethylene dropwise at about 0°C. During the reaction, control the temperature of the reaction system At 0-2°C, the dropwise addition was completed, and the reaction was carried out for 3 hours. Pour the reaction solution onto crushed ice, extract the product three times with 4 liters of n-hexane, recover the solvent, hydrolyze the product with concentrated hydrochloric acid, extract the product with benzene, recover the solvent to obtain 3,3-dimethylbutyric acid (1.14 kg, 90% yield). Add a small amount of red phosphorus to the product as a catalytic reagent. At 130 ° C, air and chlorine gas are introduced at the same time. The reaction is complete. The excess chlorine gas is removed by air, and vacuum distillation (collecting 102-109 ° C / 1mmHg) to obtain 2-chloro- 3,3-Dimethylbutanoic acid (1.31 kg, 89% yield), the chloride was dissolv...

example 2

[0031] Dissolve the swirling tertiary leucine in water, add sodium hydroxide to adjust the pH to 10, control the temperature at 0°C, slowly add acetyl chloride dropwise, and at the same time control the pH with sodium hydroxide until the ninhydrin in the reaction solution does not detect color. Add hydrochloric acid to adjust the pH to 1, and the acetylated D,L-tert-leucine product becomes crystals, which are collected by filtration.

example 3

[0033] Dissolve the swirling tertiary leucine in water, add sodium hydroxide to adjust the pH to 10, control the temperature at 0°C, slowly add chloroacetyl chloride dropwise, and at the same time control the pH with sodium hydroxide until the ninhydrin in the reaction solution is no longer detected. color. Add hydrochloric acid to adjust the pH to 1, and the chloroacetylated D,L-tert-leucine product becomes crystals, which are collected by filtration.

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Abstract

The invention discloses a method for simultaneously preparing D-tert-leucine and L-tert-leucine. The method comprises the following steps: 1, reacting n-butanol with 1,1-dichloroethylene to obtain a 3,3-dimethylbutyric acid product; 2, adding a catalyst to the 3,3-dimethylbutyric acid product, introducing air and chlorine, and carrying out a chlorination reaction to obtain 2-chloro-3,3-dimethylbutyric acid; 3, carrying out an aminolysis reaction on 2-chloro-3,3-dimethylbutyric acid to obtain D, L-tert-leucine; 4, carrying out acetylation and chloroacetylation on the obtained D, L-tert-leucine, and using L-thermal stability amino acid acylase splitting and other treatments to respectively obtain D-tert-leucine and L-tert-leucine; and 5, racemizing acetylated and chloroacetylated D-tert-leucine recovered after splitting, and carrying out cycle splitting. N-butanol and 1,1-dichloroethylene with low cost are used as initial raw materials. The cost of the method is substantially lower than that of a biological reduction method.

Description

technical field [0001] The invention belongs to the field of biocatalysis, in particular to a method for simultaneously preparing D- and L-type tertiary leucine. Background technique [0002] L-tert-leucine and D-tert-leucine are very important unnatural amino acids, and are intermediates of many drugs. Because the side chain is a tert-butyl group, it has a large steric hindrance, which is conducive to maintaining the spatial conformation after coupling with other molecules, and the amide bond formed is not easy to be recognized and degraded by enzymes in the body. At present, for the synthesis of L-tert-leucine and D-tert-leucine, in addition to the chemical resolution method, the industrial method of biocatalysis is mainly based on tert-butyl ketoacid as a substrate, and the bioreduction ammonia method is carried out with dehydrogenase. For example, "A method for preparing L-tert-leucine" 201110202325 and "A biocatalytic preparation method for D-tert-leucine" CN104513839A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/08C07C227/08C12P13/04
CPCC07C227/08C07B57/00C07B2200/07C07C51/00C07C51/363C12P13/04
Inventor 郁庆明
Owner NANJING Y BIO PHARMA CO LTD
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