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Method for biological catalytic preparing naprosyn

A technology of biocatalysis and naproxen, applied in the field of naproxen, can solve the problems of flammability, safety, low reaction rate, environmental pollution, etc., and achieve the effect of high stereoselectivity and high activity

Inactive Publication Date: 2005-02-23
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because naproxen ester is insoluble in water thereby the rate of reaction in single aqueous phase is very low; In water-organic solvent two-phase, there is the product that the pollution of organic solvent and the emulsification of organic solvent and water make again and The problem of difficult separation of substrates, and a series of safety problems caused by volatile and flammable organic solvents

Method used

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  • Method for biological catalytic preparing naprosyn

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Ionic liquid [bmim] PF 6 , and water to form a two-phase system, added to a 100 ml Erlenmeyer flask, lipase L-1754, 125 mg, and 75 mg racemic naproxen methyl ester were added to the system, and in another Erlenmeyer flask Water-isooctane constitutes a two-phase system, and the addition of the same components is compared with the water-ionic liquid two-phase system.

[0019] At 32 degrees centigrade, 170 rev / min reaction, take a sample every other day, after the remaining R-naproxen methyl ester that exists in ionic liquid phase extracts with n-hexane, adopt HP1090 type high performance liquid chromatography (HP company) chiral column (OD-H), column length 250 * 4.6 millimeters, eluent is n-hexane: Virahol is 9: 1 (volume ratio), flow velocity 0.5 milliliters / min, under room temperature condition, wavelength 254nm, measure naproxen A The corresponding excess value of the ester (ee s ); the product S-naproxen present in the aqueous phase is vacuum-dried to remove water ...

Embodiment 2

[0032] Other is the same as embodiment 1, changes the ratio of water-ionic liquid two-phase, ionic liquid: water (volume ratio) A=3: 1; B=2: 1; C=2: 2; D=2: 3; E= 2:4; at 30 degrees Celsius, 170 rpm, after 5 days of reaction, take samples for measurement. The results are shown in Table 2:

[0033] The influence of table 2 water quantity on enzyme activity

[0034] reaction system ee s (%) ee p (%) E conversion rate

[0035] (C%)

[0036] A 18.44 97.97 116.8 15.84

[0037] B 27.39 98.10 136.3 21.83

[0038] C 28.6 3 98.30 154.3 22.56

[0039] D 22.03 97.71 107.1 18.40

[0040] E 21.82 97.98 121.3 18.21

[0041] The comparison found that there was an optimal ratio of ionic liquid to water in the water-ionic liquid two-phase system, and the activity and stereoselectivity of lipase reached the maximum at this ratio.

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Abstract

A method for preparing optical pure naproxen by lipase chiral resoluted naproxen methoxycarbonyl in water-ionic liquid two-phase system is disclosed. It is carried out by taking lipase cylindrical candidiasis L-1754 as catalyst and taking racemic naproxen methoxycarbonyl as reactive substratum. It achieves three-dimensional selectivity and activity.

Description

technical field [0001] The invention relates to a method for preparing optically pure naproxen by using lipase to hydrolyze racemic naproxen methyl ester. Background technique [0002] The chemical name of naproxen is 2-(6-methoxy-2-naphthyl)-propionic acid, which belongs to 2-aryl propionic acid drugs, and is the main drug for antipyretic and analgesic, anti-inflammatory and anti-rheumatic. Its a position contains a chiral carbon atom, and there is a pair of optical isomers. Clinical studies have shown that the (s)-(+)-configuration is 28 times more active than its R-(-)-configuration. In order to improve drug efficacy, reduce drug side effects, expand drug safety range, reduce complications and correctly evaluate drugs, it is necessary to prepare optically pure drugs. And the U.S. Food and Drug Administration (FDA) promulgated a new law in 1992 to strictly limit the use of racemic drugs. It is stipulated that new drugs should be sold in the form of a single chiral isome...

Claims

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Application Information

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IPC IPC(8): C12P7/40
Inventor 辛嘉英赵永杰
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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