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Method for preparing (S)-3-butyne-2-propynylamine through biological catalysis

A technology of biocatalysis and propargylamine, applied in the field of biocatalytic chemical reactions, can solve the problems of low selectivity, cumbersome hydrogenation steps, and low conversion rate

Active Publication Date: 2021-05-11
SHANGHAI STA PHARMA R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to provide a preparation method of (S)-3-butyne-2-propynylamine with high yield, good selectivity and simplified route, which mainly solves the problem of transition metal catalysis in the existing route steps. The steps of hydrogenation of enamines or imines are relatively cumbersome, and the technical problems of low conversion rate or low selectivity

Method used

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  • Method for preparing (S)-3-butyne-2-propynylamine through biological catalysis
  • Method for preparing (S)-3-butyne-2-propynylamine through biological catalysis
  • Method for preparing (S)-3-butyne-2-propynylamine through biological catalysis

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Experimental program
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Effect test

Embodiment 1

[0054] In an 8 mL glass reaction vial, add 4 mL of ammonium chloride buffer. Add a small amount of ammonia water several times, and keep stirring with a glass rod. After the reaction solution is uniform, submerge the electrode into the reaction solution, measure the pH value of the reaction solution again, adjust the pH value to 8.5, shake the glass reaction bottle gently, and wait after the electrode is submerged in the reaction solution. After the number is stable, read it, measure it three times in parallel, and record it, and finally take the average value of the three measurements, and the pH value of the reaction solution is 8.5. After the measurement, clean the electrode with distilled water, blot the distilled water dry with filter paper, and put on the composite electrode cover, and the measurement step is completed. Then add 50mg of imine reductase lyophilized powder and 1mg of nicotinamide adenine dinucleotide phosphate (oxidized state) (NADP), 5mg of glucose dehydr...

Embodiment 2

[0060] First, add 21.40 g of ammonium chloride into 1 L of pure water, stir well until the solid is clear, and prepare 400 mmol of ammonium chloride buffer solution. The buffer concentration was measured with a pH meter, and the initial pH value was 7.5. In an 8ml glass reaction vial, add 4ml of ammonium chloride buffer. Ammonia water was added to adjust the pH value so that the reaction solution in the 8ml glass reaction bottle reached 8.5. Then add 50mg of imine reductase (AoIRED) lyophilized powder and 1mg of nicotinamide adenine dinucleotide phosphate (oxidized state) (NADP), 5mg of glucose dehydrogenase (GDH), and 100mg of glucose to the reaction solution and stir well Then 20 mg of the substrate acetylenone was added. Put it into a full-temperature constant temperature culture shaker, adjust and control the reaction temperature to 30°C, and continuously stir at a constant temperature for 24 hours to make it fully react.

[0061] Take 1ml of the reaction solution and a...

Embodiment 3

[0064] First, add 21.40 g of ammonium chloride into 1 L of pure water, stir well until the solid is clear, and prepare 400 mmol of ammonium chloride buffer solution. The buffer concentration was measured with a pH meter, and the initial pH value was 7.5. In an 8ml glass reaction vial, add 4ml of ammonium chloride buffer. Ammonia water was added to adjust the pH value so that the reaction solution in the 8ml glass reaction bottle reached 10. Then add 50mg of imine reductase (AoIRED) lyophilized powder and 1mg of nicotinamide adenine dinucleotide phosphate (oxidized state) (NADP), 5mg of glucose dehydrogenase (GDH), and 100mg of glucose to the reaction solution and stir well Then 20 mg of the substrate acetylenone was added. Put it into a full-temperature constant temperature culture shaker, adjust and control the reaction temperature to 30°C, and continuously stir at a constant temperature for 24 hours to make it fully react.

[0065] Take 1ml of the reaction solution and ad...

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Abstract

The invention discloses a method for preparing (S)-3-butyne-2-propynylamine through biological catalysis, which is characterized in that in a liquid-phase reaction system, 3-alkynyl-2-butanone is used as a substrate, and in the presence of coenzyme, carbonyl of the 3-alkynyl-2-butanone is reduced into chiral amino under the catalysis of imine reductase to prepare the (S)-3-butyne-2-propynylamine. The method has the advantages of simple operation, mild and easily-controlled reaction conditions, short reaction time, high substrate conversion rate, and high chiral purity of the obtained product.

Description

technical field [0001] The invention relates to the field of biocatalytic chemical reactions, in particular to a method for preparing enantiomerically pure (S)-3-butyne-2-propynylamine by biocatalysis. Background technique [0002] (S)-3-butyne-2-propynylamine (as shown in formula II) is a very important chiral building block, which is used in the synthesis of many pharmaceutical intermediates. For example, (S)-3-butyne-2-propynylamine is an important drug intermediate in the preparation route of drugs for inhibiting neurodegenerative diseases. [0003] [0004] At present, the method for preparing (S)-3-butyne-2-propynylamine is shown as follows, and in the literature (Chin.J.Chem.2013,31,173–181) the (R)-(+)-3-buty Alkyn-2-alcohol is used as raw material, and the highly toxic and unstable raw materials such as triphenylphosphine and hydrazine are used to undergo a one-step inversion reaction and a one-step removal reaction of the protective group to obtain the product ...

Claims

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Application Information

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IPC IPC(8): C12P13/00
CPCC12P13/001
Inventor 李杰孙丰来唐大林蔡小飞郑晨抗谢磊周丹朱景仰傅小勇陈民章
Owner SHANGHAI STA PHARMA R&D CO LTD
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