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Method for biological catalyzed synthesis of optically active alkyl lactone

An optically active, alkyl lactone technology, applied in the field of bioengineering, can solve the problems of poor catalytic synthesis effect of alkyl lactones, inability to synthesize chiral lactones, short chiral substituents, etc., and achieves good industrial application prospects , The effect of good optical purity of the product and high substrate concentration

Active Publication Date: 2015-05-27
SUZHOU BAIFUAN ENZYME TECH +2
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

et al. used chemical-enzymatic combination to catalyze the synthesis of alkyl-derived (S)-γ-valerolactone (Appl.Microbiol.Biotechnol.2013,97:3865–3873), which requires the use of two different enzyme combinations, which are costly , and the chiral substituent is a shorter methyl group, and it is impossible to synthesize chiral lactones containing long-chain alkyl substitutions
Chen Bing and others catalyzed the synthesis of 2-hydroxyl substituted chiral alkyl lactones by lactonase (Adv.Synth.Catal.2009,351:2959-2966; Chem.Commun.2010,46:2754–2756), but for 2 Catalytic synthesis of unsubstituted alkyl lactones is not effective

Method used

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  • Method for biological catalyzed synthesis of optically active alkyl lactone
  • Method for biological catalyzed synthesis of optically active alkyl lactone
  • Method for biological catalyzed synthesis of optically active alkyl lactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～6

[0029] Examples 1-6: Stereoselective reduction of 5-carbonyldecanoic acid catalyzed by wet cells of Candida parapsilosis

[0030] A method for biocatalytically synthesizing optically active alkyl lactones, the method comprising the following steps:

[0031] (1) Cell culture of Candida parapsilosis

[0032] Seed liquid medium formula: 1% glycerin, 0.5% peptone, 0.8% beef extract, pH 7.0. High temperature sterilization at 121°C for 20 minutes.

[0033] Fermentation medium formula: glycerin 15g / L, beef extract 8g / L, peptone 5g / L, KH 2 PO 4 2.0g / L, Na 2 HPO 4 2.0g / L, NaCl 0.5g / L, MgSO 4 0.5g / L, pH 7.0. High temperature sterilization at 121℃ for 20min.

[0034] Take the slant of Candida parapsilosis CGMCC2.3539 preserved at 4°C, pick a loop and inoculate it into a 250ml shake flask containing 50ml seed liquid medium. Cultivate on a shaker at 180 rpm for 24 hours at 30°C, transfer to a 500ml shaker flask containing 100ml of fermentation medium at an inoculum size of 5% (v / v),...

Embodiment 7-8

[0041] Stereoselective reduction of 4-oxodecanoic acid catalyzed by whole-cell Candida parapsilosis

[0042] Weigh an appropriate amount of wet cells of Candida parapsilosis as described in step (1) of Example 1-6, suspend in 10ml potassium phosphate buffer (100mM, pH 7.0), add 100g / L glucose and different concentrations of 4- Carbonyl decanoic acid was reacted with magnetic stirring for 12 hours, and a sample was taken to detect the reaction conversion rate.

[0043] Take 100 μl of the reaction solution containing optically active hydroxy acid, add 100 μl of sulfuric acid (20%, w / v), mix well, add 200 μl of dichloromethane for extraction, add anhydrous sodium sulfate to the extract and dry overnight, and use gas chromatography to detect , the chromatographic column is CP-Chirasil-Dex CB column, the injector and detector are both at 280°C; the column temperature is set as: 110°C for 10min, 2°C / min to 120°C for 5min, 2°C / min to 130°C Keep for 5min, 2°C / min to 140°C for 20min. ...

Embodiment 9-13

[0047] Stereoselective reduction of 5-oxodecanoic acid catalyzed by cell-free extracts

[0048] (1) Cell culture of Candida parapsilosis: the method is the same as in Examples 1-6.

[0049] (2) Candida parapsilosis cell-free extract

[0050] Weigh 5g of Candida parapsilosis wet cells as described in Example 1, suspend in 50ml of potassium phosphate buffer (100mM, pH 7.0), place the cell suspension in an ice water bath, ultrasonic power is 400W, ultrasonic 4s , with an interval of 6 seconds, counted as one cycle, and a total of 99 cycles were performed. The crushed liquid was centrifuged at 4°C and 10,000 rpm at high speed to obtain a clarified supernatant with an activity of 40 kU / L.

[0051] (3) Preparation of optically active hydroxy acids

[0052] Take an appropriate amount of the cell-free extract described in step (2), add potassium phosphate buffer (100mM, pH 7.0) to a total volume of 10ml, add 5-carbonyldecanoic acid with a final concentration of 10g / L, 20g / L glucose,...

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Abstract

The invention relates to a method for biological catalyzed synthesis of optically active alkyl lactone. The method comprises the following steps: (1) catalyzing asymmetric reduction of a carbonyl acid to synthesize optically active hydroxy acid by using a biological catalyst; (2) in an acid environment, cyclizing the optically active hydroxy acid, thereby generating an optically active lactone compound. Freshly cultured candida parapsilosis cells or a cell-free extract is adopted as the biological catalyst for catalyzing stereoselective reduction of 4-carbonyl capric acid and 5-carbonyl capric acid, and subsequently the components are cyclized in the acid environment so as to obtain the lactone compound, so that (R)-(+)-4-hexyl-4-butyrolactone and (R)-(+)-5-amyl-5-valerolactone can be efficiently prepared. Compared with the prior art, the method is easy in preparing cells of the strain and extracts of the cells, high in stereoselectivity, simple in process for catalytic preparation of (R)-(+)-4-hexyl-4-butyrolactone and (R)-(+)-5-amyl-5-valerolactone, environment-friendly, and very good in industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of bioengineering, in particular to biocatalytic conversion synthesis of optically active (R)-(+)-4-hexyl-4-butyrolactone and (R)-(+)-5-pentyl-5-pentyl lactone method. Background technique [0002] Optically active chiral lactones, such as (R)-(+)-4-hexyl-4-butyrolactone and (R)-(+)-5-pentyl-5-valerolactone, are important fragrances Additives are widely used in brewing, food manufacturing and other fields. Chemical resolution is a common method for preparing chiral lactones with high optical purity. The usual chemical resolution methods generally use racemic chiral lactones as starting materials, hydrolyze the ring-opening under alkaline conditions, and then perform esterification and alkylation. Oxygen derivatization produces a mixture of diastereoisomers, which are separated to obtain compounds of a single configuration, followed by hydrolysis and cyclization to obtain optically pure chiral lactone compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/04C12P17/06C12P17/02C12R1/72
Inventor 钱小龙白云鹏郑高伟潘江许建和
Owner SUZHOU BAIFUAN ENZYME TECH
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