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Decomposition of tert-leucine with optical activity

A technology of tert-leucine and optical activity, which is applied in the field of preparing optically pure S-tert-leucine and R-tert-leucine, achieving high selectivity, less activity reduction, and reduced production costs

Inactive Publication Date: 2007-11-21
成都威克药业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But only one configuration of optically pure tertiary leucine - (S) tertiary leucine can be obtained

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Immobilization of Aspergillus oryzae aminoacylase (EC3.5.1.14), the immobilization conditions are: the fixative contains 1% gelatin, 0.5% glutaraldehyde, 60mg of aminoacylase uses 50ml of fixative; for 2 hours. After immobilization, the enzyme activity is 2800U / g (dry immobilized enzyme), and the enzyme retention activity remains 80%.

Embodiment 2

[0029] Example 2 Add 200g of RS-tert-leucine to a 2000ml three-necked flask, add 850ml of 2N sodium hydroxide solution, and add 240g of acetyl chloride in 400ml of acetone solution dropwise with stirring in an ice bath. The temperature does not exceed 20°C. After the addition, react for 2 hours, concentrate to remove acetone, neutralize with 6N hydrochloric acid solution to pH = 4, extract three times with 1000ml ethyl acetate, combine ethyl acetate, dry over anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, and obtain RS - phenylacetyl tert-leucine 305g, yield 85%.

Embodiment 3

[0030] Example 3 In a 2000ml reaction flask, add 120g (510.6mmol) of RS-phenylacetyl-tert-leucine and 1500ml of water from Example 2, immobilize 10-30g of Aspergillus oryzae aminoacylase, and selectively hydrolyze and remove S- The phenylacetyl group of phenylacetyl-tert-leucine generates S-tert-leucine, the reaction temperature is 37°C, and the reaction time is 6 hours; the immobilized enzyme is separated by filtration, and the unreacted R-phenylacetyl group is extracted with 3×300ml ethyl acetate tert-leucine, the aqueous phase was concentrated and crystallized to obtain 63g of S-tert-leucine, with a yield of 96% and an optical purity of 99.2% ee; ethyl acetate was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain R-phenylacetyl Base tert-leucine.

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Abstract

A method for disassembling optical active tertiary leucine is carried out by reacting RS-tertiary leucine with phenacerine to generate RS-phenyl tertiary leucine, selectively hydrolyzing for phenyl of S-phenyl tertiary leucine to generate S-tertiary leucine by fixed Aspergillus oryzae amino acidylating enzyme, adding into organic solvent, phase-split separating for inactivated R-phenyl tertiary leucine, concentrating for S-tertiary leucine in aqueous-phase, crystallizing, adding acid into R-phenyl tertiary leucine in oil-phase, hydrolyzing to obtain R-tertiary leucine. It's cheap and simple and has no environmental pollution.

Description

technical field [0001] The invention relates to a method for splitting and preparing optically pure S-tert-leucine or R-tert-leucine from the racemate of tert-leucine. More specifically, the present invention relates to a method for splitting and preparing optically pure S-tert-leucine and R-tert-leucine from derivatized racemic tert-leucine by biological enzymes. Background technique [0002] Tert-leucine is a non-proteinogenic chiral amino acid, an important pharmaceutical intermediate, and widely used in chiral synthesis and peptide synthesis. [0003] The synthesis of optically pure tertiary leucine mainly includes chemical synthesis and biological enzymatic method, and there are two methods of biological enzymatic method, enzymatic catalysis and enzymatic resolution. There are detailed reports in the literature such as "Amino Acids and Biological Resources" (2003, 25(4), 14-19). [0004] The commonly used resolution method for tertiary leucine is: [0005] Underivati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/06C12P41/00
Inventor 王德祥吴松福王丽杰袁莉李主全
Owner 成都威克药业有限责任公司
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