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Method for preparing S-(+)-3-hydroxy tetrahydrofuran through microbial conversion

A technology for hydroxytetrahydrofuran and microbial transformation, applied in the direction of fermentation, etc., can solve the problems of cumbersome preparation process of chiral catalyst, difficult separation and extraction, and unsuitable for industrial production, and achieves easy large-scale industrial production, easy large-scale cultivation, The effect of improving the molar conversion rate

Active Publication Date: 2012-12-12
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In literature reports, the synthesis of (S)-(+)-3-hydroxytetrahydrofuran can be obtained by asymmetric hydroboration or hydrosilation of dihydrofuran, which requires a chiral catalyst. The preparation process of the chiral catalyst is cumbersome and expensive; it can be obtained by 4 -Preparation by asymmetric hydrogenation-reduction-intramolecular etherification of chloro-3-carbonyl butyrate, the method has high cost and is not suitable for industrial production; it can be prepared by enzymatic resolution of 3-hydroxytetrahydrofuran racemate, enzyme The highest resolution efficiency of the resolution method can only reach 50%, and the production efficiency is low; it can be synthesized by reduction-intramolecular etherification of malic acid, but this method needs to reduce the malic acid diester with expensive lithium aluminum hydride, and Requires protection of secondary hydroxyl to prevent racemization
In most cases, the optical purity of the product in the above-mentioned preparation method is not enough, or there are factors that are not conducive to industrial production such as separation and extraction difficulties

Method used

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  • Method for preparing S-(+)-3-hydroxy tetrahydrofuran through microbial conversion
  • Method for preparing S-(+)-3-hydroxy tetrahydrofuran through microbial conversion
  • Method for preparing S-(+)-3-hydroxy tetrahydrofuran through microbial conversion

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Inoculate CGMCC No.2266 bacteria into the slant medium, and culture at 30°C for 4-6 days to obtain the slant of bacteria. Use an inoculation needle to take an inoculation loop from the slant of the bacterium and inoculate it into a 250mL Erlenmeyer flask containing 100mL of liquid medium, and incubate at 30°C and 180r / min for 24h to obtain a seed solution. Inoculate 10 mL of seed solution (inoculum volume fraction 10% of the medium) into a 250 mL Erlenmeyer flask containing 100 mL of liquid medium, cultivate it for 24 hours at 30°C and 180 r / min to obtain a fermented liquid, centrifuge the fermented liquid, Obtain enzyme-containing bacterial cells.

[0035] The determination of the dry weight of the bacteria is to take a small part of the wet bacteria containing the enzyme cells after centrifuging the fermentation broth, and dry it at 120°C for 48 hours to a constant weight, measure the weight of the dry cells, and calculate the unit content of the fermentation broth. ...

Embodiment 2

[0041] Inoculate CGMCC No.2266 bacteria into the slant medium, and culture at 30°C for 4-6 days to obtain the slant of bacteria. Use an inoculation needle to take an inoculation loop from the slant of the bacterium and inoculate it into a 250mL Erlenmeyer flask containing 100mL of liquid medium, and incubate at 30°C and 180r / min for 24h to obtain a seed solution. Inoculate 10 mL of seed solution (the inoculation amount is based on 10% of the volume of the medium used) in a 250 mL Erlenmeyer flask containing 100 mL of liquid medium, cultivate it for 24 hours at 30°C and 180 r / min to obtain a fermentation liquid, and centrifuge the fermentation liquid to obtain Enzyme-containing bacterium cells, the dry weight of enzyme-containing bacterium cells per liter of fermentation broth is 50 grams.

[0042] Add the wet cells obtained after centrifugation of the above 200 ml fermentation broth to ten portions of Erlenmeyer flasks each containing 100 mL pH7.0 phosphate buffer solution, wh...

Embodiment 3

[0048] Saccharomyces cerevisiae CGMCC No.2266 strain was inoculated into the slant medium, and cultured at 30° C. for 4 to 6 days to obtain the slant surface of the bacteria. Use an inoculation needle to take an inoculation loop from the slant of the bacterium and inoculate it into a 250mL Erlenmeyer flask containing 100mL of liquid medium, and incubate at 30°C and 180r / min for 24h to obtain a seed solution. Inoculate 10 mL of seed solution (the inoculation amount is based on 10% of the volume of the medium used) in a 250 mL Erlenmeyer flask containing 100 mL of liquid medium, cultivate it for 24 hours at 30°C and 180 r / min to obtain a fermentation liquid, and centrifuge the fermentation liquid to obtain Enzyme-containing bacterium cells, the dry weight of enzyme-containing bacterium cells per liter of fermentation broth is 50 grams.

[0049] Add the wet cells obtained after centrifugation of the above-mentioned 200 milliliters of fermentation broth to five parts of Erlenmeyer...

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Abstract

The invention discloses a method for preparing S-(+)-3-hydroxy tetrahydrofuran through microbial conversion. The method comprises the following steps of: performing conversion reaction at the temperature of between 25 and 45 DEG C for 8 to 40 hours in phosphate buffer with pH of 5.0 to 8.0 by taking 3-keto-tetrahydrofuran as a substrate, and an enzyme-containing bacteroid cell obtained through the fermentation of saccharomyces cerevisiae CGMCC No.2266 as a biocatalyst, and after the reaction is finished, separating and purifying conversion liquid to obtain the S-(+)-3-hydroxy tetrahydrofuran.The method has the advantages that: (1) production strains are safe and non-toxic, can be cultured in a large scale easily and are low in cost; (2) the method is easy to operate, coenzyme which is high in price is not needed to be added in the reaction process and the yield is high; (3) large-scale industrial production is easy to realize; and (4) reaction conditions are mild and the method is environmental-friendly.

Description

(1) Technical field [0001] The invention relates to a method for preparing S-(+)-3-hydroxytetrahydrofuran by microbial transformation, in particular to a method for preparing S-(+)-3-hydroxytetrahydrofuran with Saccharomyces cerevisiae CGMCC No.2266 as a biocatalyst and 3-ketotetrahydrofuran as a substrate A new method for (S)-(+)-3-hydroxytetrahydrofuran. (2) Background technology [0002] (S)-(+)-3-Hydroxytetrahydrofuran ((S)-(+)-3-Hydroxytetrahydrofuran), CAS accession number: 86087-23-2, molecular formula C 4 h 8 o 2 , molecular weight 88.11. (S)-(+)-3-Hydroxytetrahydrofuran is an important intermediate in the synthesis of AIDS drug Amprenavir. After introducing (S)-(+)-3-hydroxytetrahydrofuran group into the diphenyl ether herbicide pesticide, the herbicidal activity and selectivity of the diphenyl ether herbicide can be obviously improved. [0003] In literature reports, the synthesis of (S)-(+)-3-hydroxytetrahydrofuran can be obtained by asymmetric hydroboration ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/14
Inventor 欧志敏沈文和隋志红陈庆美
Owner ZHEJIANG UNIV OF TECH
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