Method for preparing optical pure 1-(1-naphthyl)ethylamine through resolution with immobilized enzyme process

An immobilized enzyme and naphthyl technology, applied in fermentation and other fields, can solve the problems of poor resistance to organic solvents and low reusability of immobilized enzymes, and achieve excellent splitting effect and high reusability

Inactive Publication Date: 2015-05-20
南京普瑞特生物科技有限公司
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  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to solve the problems of poor organic solvent resistance and low reutilization rate of immobilized enzymes in the prior art, and provide an immobilized enzyme method with good organic solvent resistance stability and high reutilization rate. Method for resolution and preparation of optically pure 1-(1-naphthyl)ethylamine

Method used

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  • Method for preparing optical pure 1-(1-naphthyl)ethylamine through resolution with immobilized enzyme process
  • Method for preparing optical pure 1-(1-naphthyl)ethylamine through resolution with immobilized enzyme process
  • Method for preparing optical pure 1-(1-naphthyl)ethylamine through resolution with immobilized enzyme process

Examples

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example 1）

[0024] This example is the preparation method of cross-linked Candida antarctica lipase B aggregates (hereinafter referred to as cross-linked enzyme aggregates):

[0025] 15 mg of Candida antarctica lipase B (hereinafter abbreviated as CLAB) was added to 5 mL of water and dissolved completely to obtain an enzyme liquid.

[0026] Then add 25mL of saturated ammonium sulfate solution to precipitate the enzyme protein from the enzyme solution.

[0027] Then add 0.15mL of 25wt% glutaraldehyde aqueous solution, stir and crosslink for 2h.

[0028] Finally, 15 mg of cross-linked enzyme aggregates were obtained by dialysis and freeze-drying.

example 2～ example 5）

[0030] The method of each example is basically the same as Example 1, see the difference Table 1 .

[0031] Table 1

[0032]

Embodiment 1）

[0034] The method for preparing optically pure 1-(1-naphthyl)ethylamine by immobilized enzymatic resolution in this embodiment has the following steps:

[0035] ①In 5 mL of n-hexane solvent, add 5 mg of the cross-linked enzyme aggregate prepared in Example 1 and 171.2 mg of 1-(1-naphthyl)ethylamine racemate (1.0 mmol, hereinafter referred to as racemate) , the temperature of the reaction system was raised to 40°C, and 5 mL of n-hexane solvent containing 86 mg of vinyl acetate (1.0 mmol) was added to the reaction system within 1.5 h. A mixture of 1-(1-naphthyl)ethylamine ester and (S)1-(1-naphthyl)ethylamine.

[0036] ② After the cross-linked enzyme aggregates were separated by filtration, they were distilled under reduced pressure to obtain light yellow oil.

[0037] Using petroleum ether and isopropanol (1:1) as the mobile phase, the oil was separated by column chromatography to obtain (R)1-(1-naphthyl)ethylamino ester and 83.0 mg of (S)1-( 1-Naphthyl)ethylamine, yield 48.5...

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Abstract

The invention discloses a method for preparing optical pure 1-(1-naphthyl)ethylamine through resolution with immobilized enzyme process. The method comprises the following steps of selectively esterifying (R)-1-(1-naphthyl)ethylamine in 1-(1-naphthyl)ethylamine racemate, then separating (R)-1-(1-naphthyl)ethylamine esterified compound from (S)-1-(1-naphthyl)ethylamine to obtain (S)-1-(1-naphthyl)ethylamine, and finally hydrolyzing the (R)-1-(1-naphthyl)ethylamine compound to obtain the (R)-1-(1-naphthyl)ethylamine. The catalyst for selective esterification is crosslinked Candida antarctica lipase B aggregate which is prepared through the following steps of dissolving Candida antarctica lipase B in water to obtain enzyme solution, depositing zymoprotein from the enzyme solution with a precipitator, then adding a difunctional crosslinking agent for crosslinking, and drying. The crosslinked enzyme aggregate is high in repeated utilization rate, and has relatively strong operation stability in a pure organic solvent.

Description

technical field [0001] The invention relates to a biological resolution method, in particular to a method for preparing optically pure 1-(1-naphthyl)ethylamine through resolution by an immobilized enzyme method. Background technique [0002] Optically pure 1-(1-naphthyl)ethylamine has two configurations, namely (S)-1-(1-naphthyl)ethylamine and (R)-1-(1-naphthyl)ethylamine, in which (S)-1-(1-naphthyl)ethylamine is a high-efficiency resolving agent for the resolution of amino acid acetylated derivatives, and (R)-1-(1-naphthyl)ethylamine can not only be used as a resolving agent, And it is an important pharmaceutical intermediate. [0003] At present, the methods for preparing optically pure 1-(1-naphthyl)ethylamine mainly include the following categories: [0004] (1) Asymmetric synthesis: as disclosed in the international patent document WO2004110976A2, 1-(1-naphthyl)ethanone is used as a raw material, and first catalytically hydrogenated to (R)-α-naphthyl alcohol under the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/00
Inventor 汪斌马迪张春勇胡秀英舒莉朱炳龙
Owner 南京普瑞特生物科技有限公司
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