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Biological preparation method of chiral hydroxy acid ester

A hydroxy acid ester and biological preparation technology, applied in the direction of using vectors to introduce foreign genetic material, oxidoreductase, recombinant DNA technology, etc., can solve problems such as difficulty and pollution, and achieve high efficiency, improved chiral selectivity, The effect of simple process

Active Publication Date: 2020-07-28
黄山科宏生物香料股份有限公司
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  • Abstract
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Problems solved by technology

Traditional chemical synthesis is characterized by great difficulty and pollution

Method used

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  • Biological preparation method of chiral hydroxy acid ester

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Embodiment 1

[0019] A biological preparation method of a chiral hydroxy acid ester, comprising the following steps:

[0020] (1) The fatty acid is oxidized by ketolase globene monooxygenase to generate 4-oxo fatty acid;

[0021] (2) 4-oxo fatty acid was asymmetrically reduced by short-chain dehydrogenase PpYSDR-M85Q / L136A to obtain R-hydroxy acid ester.

[0022] Among them, the ketolase spheroidene monooxygenase is EC 1.14.15.9-spheroidene monooxygenase, which contains heme, participates in the biosynthesis of cyclin and 2,2'-dioxy-spiroflavin, and is derived from Rhodobactercapsulatus, Rhodobacter sphaeroides, Rhodovulum sulfidophilum, Rubrivivax gelatinosus.

[0023] Wherein the step 2 reaction is shown in the following formula:

[0024]

[0025] The short-chain dehydrogenase PpYSDR-M85Q / L136A is produced by mutation transformation of the wild-type short-chain dehydrogenase PpYSDR, which specifically includes the following process:

[0026] Mutant construction:

[0027] The oligon...

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Abstract

The invention discloses a biological preparation method of a chiral hydroxy acid ester. The method comprises the following steps: (1) oxidizing a fatty acid by ketolase spheroidene monooxygenase to generate a 4-oxo fatty acid; and (2) asymmetrically reducing the 4-oxo fatty acid by short-chain dehydrogenase PpYSDR-M85Q / L136A to obtain an R-hydroxy acid ester. In the biological preparation method of a chiral hydroxy acid ester of the invention, a short-chain dehydrogenase mutant is constructed, the short-chain dehydrogenase mutant greatly improves the activity and chiral selectivity for keto acids compared with the wild type, the efficiency of the enzyme in catalyzing keto acids to prepare chiral lactones can be improved, and thereby an application value of the enzyme is fully explored. Atthe same time, the enzymatic synthesis of the chiral hydroxy acid ester has the characteristics such as simple process, environmental friendliness, and high benefit.

Description

technical field [0001] The invention belongs to the technical field of biochemical industry, and in particular relates to a biological preparation method of chiral hydroxy acid ester. Background technique [0002] The two enantiomers of chiral compounds often have different efficacies or their effects are very different. Therefore, the synthesis of single enantiomers has attracted more and more attention. Optically active chiral lactones are widely used in chiral natural fragrances. Traditional chemical synthesis is characterized by great difficulty and pollution. Fatty acids can be oxidized by ketoacids to obtain ketoacids. The asymmetric reduction of ketoacids is an important method for preparing optically active chiral hydroxyacids. In theory, 100% of the substrate ketoacids can be converted into chiral hydroxyacids of a single enantiomer, which has high industrial application value. Compared with chemical asymmetric reduction, biocatalysis has advantages in chemoselec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/62C12N9/04C12N15/70
CPCC12P7/62C12N9/0006C12N15/70
Inventor 于洪巍贾卫民王之建俞鑫焱洪一鸣程存照
Owner 黄山科宏生物香料股份有限公司
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