Method for synthesizing lactam compound

A technology of artificial synthesis of lactam compounds, applied in the direction of fermentation, etc., can solve the problems of unstable structure, expensive metal catalysts, high reaction temperature, etc., and achieve high substrate specificity and high catalytic efficiency without being limited by light conditions Effect

Pending Publication Date: 2021-04-23
NANJING UNIV OF TECH
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

Hollmann and his research group reported a method for the preparation of lactams by coupling amino alcohols with two enzymes. Horse liver alcohol dehydrogenase catalyzed amino alcohols to generate lactam compounds, but NADH oxidase from Streptococcus mutans (SmNOX) in situ RNAD + , the structural instability of NOXs hinders the application of technological scale
[0004] In summary, although some synthetic methods are relatively efficient, they have disadvantages such as expensive metal catalysts, polluting the environment, using toxic solvents, harsh reaction conditions, high reaction temperatures, and unstable structures of enzymatically regenerated catalysts.

Method used

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  • Method for synthesizing lactam compound
  • Method for synthesizing lactam compound
  • Method for synthesizing lactam compound

Examples

Experimental program
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Effect test

Embodiment 1

[0075] Regenerated NAD with 7-trifluoromethyl-N1,N10-vinylisoalloxazine chloride + Catalyst, coupled with horse liver alcohol dehydrogenase to catalyze 1-amino-4-butanol to 2-oxo-4-butyrolactam and H 2 o 2 , catalase further converts H 2 o 2 catalytic decomposition to H 2 O and O 2 .

[0076] Its reaction schematic diagram is as follows figure 1 As shown, 1-amino-4-butanol was catalyzed by horse liver alcohol dehydrogenase, 7-trifluoromethyl-N1,N10-vinylisoxazine chloride and NAD + Under the regeneration reaction system constituted, the lactamization product 2-oxo-4-butyrolactam and H 2 o 2 , catalase further converts H 2 o 2 catalytic decomposition to H 2 O and O 2 .

[0077] In 10 mL of 50 mM pH 8 potassium phosphate buffer, 1-amino-4-butanol 20 mM, NAD + 1mM, 7-trifluoromethyl-N1, N10-vinylisoalloxazine chloride 0.5mM, horse liver alcohol dehydrogenase 5U / mL, catalase 20U / mL, the reaction solution is connected with the outside air, in 30° C., 200 rpm shaker, ...

Embodiment 2

[0080] 7-Trifluoromethyl-N1,N10-vinylisoalloxazine chloride as regenerated NAD + Catalyst, coupled with horse liver alcohol dehydrogenase to catalyze 4-amino-2-methyl-1-butanol to (R)-3-methylpyrrolidone-2-one and H 2 o 2 , catalase further converts H 2 o 2 catalytic decomposition to H 2 O and O 2 .

[0081] In 10 mL of 50 mM pH 8 potassium phosphate buffer, 4-amino-2-methyl-1-butanol 20 mM, NAD + 1mM, 7-trifluoromethyl-N1, N10-vinylisoalloxazine chloride 0.5mM, horse liver alcohol dehydrogenase 5U / mL, catalase 20U / mL, the reaction solution was communicated with the outside air, in 30° C., 200 rpm shaker, reacted for 24 hours, and by gas phase quantitative analysis, the yield of (R)-3-methylpyrrolidone-2-one represented by formula III-II was 95%.

[0082]

Embodiment 3

[0084] 7-Trifluoromethyl-N1,N10-vinylisoalloxazine chloride as regenerated NAD + Catalyst, coupled with horse liver alcohol dehydrogenase to catalyze 1-amino-5-hydroxypentane to 5-aminovaleric acid lactam and H 2 o 2 , catalase further converts H 2 o 2 catalytic decomposition to H 2 O and O 2 .

[0085] In 10 mL of 50 mM pH 8 potassium phosphate buffer, 1-amino-5-hydroxypentane 20 mM, NAD + 1mM, 7-trifluoromethyl-N1, N10-vinylisoalloxazine chloride 0.5mM, horse liver alcohol dehydrogenase 5U / mL, catalase 20U / mL, the reaction solution was communicated with the outside air, in 30° C., 200 rpm shaker, reacted for 12 hours, and by gas phase quantitative analysis, the yield of 5-aminovalerolactam represented by formula III-III was 35%.

[0086]

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Abstract

The invention discloses a method for synthesizing a lactam compound. Amino alcohol, alcohol dehydrogenase, flavin molecules, cofactors and catalase react in a solvent. The invention constructs a green and environment-friendly method for enzymatic synthesis of the lactam compound. Compared with common toxic chemical catalysts, the alcohol dehydrogenase is selected as a catalyst, the method has the characteristics of high substrate specificity, no pollution, high catalytic efficiency and the like, the solvent is a buffer aqueous solution, no toxic solvent is used, no by-product is generated, and the product is easy to separate.

Description

technical field [0001] The invention belongs to the field of biochemical industry, in particular to an artificial flavin analog to regenerate NAD + A method for generating lactam compounds by catalyzing the oxidation of amino alcohols by coupled horse liver alcohol dehydrogenase. Background technique [0002] Lactam is an important class of organic molecular framework, which exists in many natural products and drug molecules, and has potential biological activity and medicinal value. Lactam compounds refer to cyclic compounds containing amide bonds in the molecule, including β-, γ-, δ-lactams, etc., which are not only precious intermediates in organic synthesis, but also many natural products or drugs with biological activity. Molecular core skeleton. In addition, as a nitrogen-containing organic heterocyclic compound, lactam is also an important chemical raw material. Therefore, the synthesis of lactams has always been a hot spot in the chemical community and has importa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/10C12P17/12
CPCC12P17/10C12P17/12
Inventor 应汉杰朱晨杰付亚萍庄伟谭卓涛张肖旺李明柳东牛欢青
Owner NANJING UNIV OF TECH
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