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Method for splitting optically pure 2-octyl alcohol by adopting enzyme catalysis

A technology of octanol and octanol ester, which is applied in the field of R-2-octanol, can solve the problems of low space-time yield, loss of economic feasibility, low loading ratio of substrate and enzyme, and achieve low cost, easy separation, and easy The effect of industrialization

Inactive Publication Date: 2013-09-18
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The immobilized enzyme prepared by common carrier, because the carrier occupies a large proportion, is generally 99.9% to 90% of the immobilized enzyme by mass (Cao, L.Q., Langen, L.V., Sheldon, R.A., 2003. Immobilised enzymes: carrier -bound or carrier-free? Curr.Opin.Chem.Biol.14,387-394), which "dilutes" the activity of the enzyme so that the ratio of substrate to enzyme loading tends to be low, which further leads to low space-time yields (Tischer ,W.,Kasche,V.,1999.Immobilized enzymes:crystals or carriers?Trends Biotechnol.17,326-335), so that the enzyme-catalyzed process loses economic viability (because of the typical enzyme-catalyzed process, the loading ratio of substrate and enzyme is at least 20. Only meaningful (Luetz, S., Giver, L., Lalonde, J., 2008. Engineered enzymes for chemical production. Biotechnol. Bioeng. 101, 647–653)

Method used

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  • Method for splitting optically pure 2-octyl alcohol by adopting enzyme catalysis
  • Method for splitting optically pure 2-octyl alcohol by adopting enzyme catalysis
  • Method for splitting optically pure 2-octyl alcohol by adopting enzyme catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In a 25ml Erlenmeyer flask with a stopper, add 10ml of n-hexane, 1mmol of racemic 2-octanol (purchased from Sigma, the same below), 2mmol of vinyl acetate, and 0.1g of immobilized enzyme immobilized by macroporous resin. And 10μL of 0.1mol / L phosphate buffer with pH=8. The reaction mixture was placed on a shaker at 30° C., and was shaken and reacted at a constant temperature at a speed of 150 rpm for 20 hours. 1 microliter of the reaction mixture was taken for gas chromatography analysis. The analysis method was as follows:

[0035] The chiral column was G-TA Capillary Column (40m×0.25mm×0.12μm, Astech, USA), and the temperature of the column oven, injection port and detector were 110°C, 200°C and 250°C, respectively. Nitrogen was used as the carrier gas with a flow rate of 40 mL / min and a split ratio of 1:20.

[0036] The above samples were analyzed and the results were as follows: figure 1 Shown, YLL lipase preferentially catalyzes the R-isomer, and reaction 20 hour...

Embodiment 2

[0043] In a 25ml Erlenmeyer flask with a stopper, add 10ml of n-hexane, 1mmol of racemic 2-octanol, 2mmol of succinic anhydride, 0.1g of immobilized enzyme immobilized by macroporous resin and 10μL of 0.1mol / L pH=8 Phosphate buffer. The reaction mixture was placed on a shaker at 30°C, and was shaken and reacted at a constant temperature at 150 rpm for 20 hours. Take 1 microliter of the reaction mixture and detect it under the same conditions as in Example 1. The result is the conversion rate c is 0.51, and the stereoselectivity of the enzyme is E=150.

[0044] The above reaction mixture was extracted with an equal volume of 1 mol / L sodium carbonate solution to obtain S-2-octanol and R-2-octanol succinate.

[0045] In order to further hydrolyze the obtained R-2-octanol succinate to generate R-2-octanol, an aqueous sodium hydroxide solution with pH=11 is used as a catalyst to catalyze the hydrolysis.

Embodiment 3

[0047]In a 25ml Erlenmeyer flask with a stopper, add 10ml of n-hexane, 1mmol of racemic 2-octanol, 2mmol of hexanoic acid, 0.1g of immobilized enzyme immobilized by macroporous resin and 20μL of 0.1mol / L pH=8 Phosphate buffered saline and 1 g of silica gel. The reaction mixture was placed on a shaker at 30°C, and was shaken and reacted at a constant temperature at 150 rpm for 20 hours. Take 1 microliter of the reaction mixture and detect it under the same conditions as in Example 1. The result is the conversion rate c is 0.43, and the stereoselectivity of the enzyme is E=135.

[0048] The above reaction mixture was passed through a silica gel chromatography column, eluted with a mixed solution of ethyl acetate and chloroform (v / v=1:1), and collected in sections to obtain S-2-octanol and R-2-octanol-hexyl ester.

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Abstract

The invention provides a novel method for preparing optically pure 2-octyl alcohol and multiple R-2-octyl alcohol esters by catalysis. The method provided by the invention comprises the following steps of: carrying out transesterification on racemization 2-octyl alcohol and ester or anhydride by utilizing extracellular lipase from Yarrowia lipolytica, and esterfying racemization 2-octyl alcohol and fatty acid to obtain S-2-octyl alcohol and R-2-octyl alcohol ester. The invention further relates to a method for preparing R-2-octyl alcohol by hydrolyzing R-2-octyl alcohol ester.

Description

technical field [0001] The invention belongs to the field of biotechnology, and relates to a method for preparing optically pure 2-octanol and R-2-octanol esters by using lipase, more specifically, it relates to using lipase to catalyze the resolution of racemic 2-octanol to prepare A method for obtaining S-2-octanol and R-2-octanol esters with high optical purity and further hydrolyzing R-2-octanol esters into R-2-octanol. Background technique [0002] Optically pure 2-octanol, also known as optically pure 2-octanol, including S-2-octanol and R-2-octanol, and their esters are important optically active drugs such as synthetic steroids, vitamin E and biopesticides and important intermediates of pesticides. Optically pure 2-octanol is also an important chiral material for preparing high-performance liquid crystals and liquid crystal devices. At present, the main methods for preparing optically pure 2-octanol include chemical methods (Ma Hongyi, 2004. Research on the prepara...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P7/18C12P7/62
Inventor 刘春朝刘英
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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