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Preparation method of optically active phenyl glycidol and derivatives thereof

A phenylglycidol, optically active technology, applied in the field of biochemistry, can solve problems such as unfavorable production process, waste of resources, cumbersome splitting steps, etc., to improve utilization rate, improve utilization, avoid metal catalysts and organic reagents pollution effect

Inactive Publication Date: 2012-02-01
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since this type of compound has two chiral centers, the yield is only 1 / 4 of the input raw material, which greatly wastes resources, and the resolution steps are cumbersome and not conducive to the production process

Method used

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  • Preparation method of optically active phenyl glycidol and derivatives thereof
  • Preparation method of optically active phenyl glycidol and derivatives thereof
  • Preparation method of optically active phenyl glycidol and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～7E

[0015] Embodiment 1~7E.coli (pETAB) selectively catalyzes (±)-1-phenyl-2-propenol epoxidation

[0016]

Embodiment 1

[0018] The expression strain E.coli (pETAB) constructed according to the method described in the patent "A Styrene Cyclooxygenase Gene and Its Use" is preserved on the LB plate (kanamycin resistance), and the E.coli (pETAB) is picked ) single bacterium colony, at 37 ℃ in the LB medium containing kanamycin (501 μ g / ml), 230rpm culture 16h as seed culture medium, inoculate in TB medium with 1% inoculum size, 37 ℃ shaking culture 3h, Then lower the temperature to 20°C to induce the expression of the styAB gene, and after 18-21 hours of induction, refrigerate and centrifuge at 4°C to harvest the bacteria.

[0019] Take 2 g of freshly cultured wet cells of E. coli (pETAB), suspend in 20 mL of potassium phosphate buffer (0.1 M, pH 7.0), and add 12 mg of (±)-1-phenyl-2-propenol. The reaction was shaken on a shaker (30° C., 230 rpm) for 2 hours. After the reaction was completed, the reaction liquid was centrifuged (8500 rpm, 5 min, 4° C.). The supernatant was extracted with ether (2×...

Embodiment 2

[0026]The reaction temperature is 20°C, the substrate is 20 mg, and the conversion takes 24 hours. Other operations are as in Example 1, and all 10 mg of (S)-1-phenyl-2-propenol can be converted into (1R,2R)-1-phenyl- 2,3-Glycidyl alcohol, and residual (R)-1-phenyl-2-propenol.

[0027] The product data is the same as in Example 1.

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Abstract

The invention belongs to the technical field of biochemistry, and discloses a preparation method of optically active (1R,2R)-1-phenyl-2,3-glycidol and derivatives thereof. According to the invention, (+-)-1-phenyl-2-allyl alcohol and derivatives thereof are adopted as substrates, E.coli pETAB whole resting cells containing styrene monooxygenase gene are adopted as a catalyst, and asymmetric epoxidations of (S)-1-phenyl-2-allyl alcohol and derivatives thereof are selectively catalyzed, such that optically pure (1R,2R)-1-phenyl-2,3-glycidol and derivatives thereof are obtained. The method provided by the invention has advantages of high raw material utilization rate, and no environmental pollution. The method is easy to be applied in industrialized productions.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and discloses a whole cell selective catalysis of (S)-1-phenyl-2-propenol and its Asymmetric epoxidation of derivatives to prepare optically active (1R,2R)-1-phenyl-2,3-glycidyl alcohol and its derivatives. Background technique [0002] Optically pure glycidyl compounds are important intermediates for the synthesis of β-receptor inhibitor drugs. In recent years, the research on the synthesis methods of these compounds has made great progress. Wherein Sharpless asymmetric epoxidation is an important method of chemical catalysis (Martin V.-S., et al.Sharpless Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation. A route to substances of absolute enantiomeric purity? J.Am.Chem. Soc., 1981,103 (20): 6237-6240), this method can obtain optically pure glycidol compound, but this catalytic reaction process needs metal catalyst, has increased production cost, also can remai...

Claims

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Application Information

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IPC IPC(8): C12P17/02C12R1/19
Inventor 吴中柳林晖刘艳
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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