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Butyryl glutamic acid derivative as well as composition and application thereof

A technology of butyryl glutamic acid and derivatives, which is applied in the field of preparation of animal feed additives or feed, and can solve the problems of mutagenesis, urinary tract disorders, and large side effects

Active Publication Date: 2018-06-29
GUANGZHOU INSIGHER BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The general feed additives commonly used in this field, which can efficiently and stably improve feed utilization and improve animal production performance, mainly include high-dose copper, high-dose zinc, feed antibiotics, chemically synthesized antibacterial agents, etc. However, these substances are used in the breeding industry Medium and long-term use has relatively large side effects, such as animal liver and kidney toxicity, growth inhibition, kidney function damage, urinary tract disorders, teratogenicity, mutagenicity, drug resistance, drug residues, and environmental pollution.

Method used

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  • Butyryl glutamic acid derivative as well as composition and application thereof
  • Butyryl glutamic acid derivative as well as composition and application thereof
  • Butyryl glutamic acid derivative as well as composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Embodiment 1 butyryl glutamic acid

[0112]

[0113] In a 2L three-necked flask, 200.34g (1.36mol, 1eq) of L-glutamic acid and 850mL (136.00g, 3.40mol, 2.5eq) of 4M NaOH aqueous solution were added successively, and after stirring at room temperature for 0.5 hours, 215.44g of butyric anhydride ( 1.36mol, 1eq.), and then added dropwise 4M NaOH aqueous solution to adjust the pH to 8-9, and TLC monitored the reaction to the end. Concentrated hydrochloric acid was added dropwise to the reaction solution to adjust the pH to 2-3, extracted with ethyl acetate (1L×3), and the organic phases were combined. The organic phase was washed with saturated brine (1L×3), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product as a colorless transparent liquid, which was cooled to 0°C for crystallization, filtered with suction, and the filter residue was washed with n-heptane (100mL× 3) The product (butyryl glutamic acid) was dried und...

Embodiment 2

[0114] Embodiment 2 N-butyryl-L-glutamic acid diethyl ester

[0115]

[0116] Step 1: Synthesis of L-glutamic acid diethyl ester hydrochloride

[0117]Add 320mL of absolute ethanol (5.48mol, 40eq) to a 1000mL single-necked bottle, cool to minus 10°C, and slowly add 28mL of thionyl chloride (378.92mmol, 2.8eq) dropwise into the reaction system. After the dropwise addition, the reaction solution was stirred and reacted at a constant temperature of minus 10° C. for 1 hour, and then 20.08 g (136.48 mmol, 1 eq) of L-glutamic acid was added to the reaction system. The reaction solution was stirred at room temperature for 2 hours, then heated to 80° C. for reaction, and monitored by TLC until the end point. The reaction liquid was concentrated under reduced pressure to remove the solvent, cooled and crystallized in the refrigerator, added ethyl acetate (150mL×3) to wash, separated by suction filtration, and dried to obtain the product (diethyl L-glutamate hydrochloride) as a whit...

Embodiment 3

[0120] Example 3 N-butyryl-L-glutamic acid bis-n-butyl ester

[0121]

[0122] Step 1: Synthesis of L-glutamic acid bis-n-butyl ester hydrochloride

[0123] Add 403.03g (5.44mol, 40eq) of n-butanol to a 1000mL single-necked bottle, cool to minus 10°C, and slowly add 45.28g (380.62mmol, 2.8eq) of thionyl chloride dropwise into the reaction system. After the dropwise addition, the reaction solution was stirred and reacted at a constant temperature of minus 10° C. for 1 hour, and then 20.00 g (135.93 mmol, 1 eq) of L-glutamic acid was added to the reaction system. The reaction solution was stirred at room temperature for 2 hours, then heated to 85° C. for reaction, and monitored by TLC until the end point. The reaction solution was concentrated under reduced pressure to remove the solvent, cooled and crystallized in the refrigerator, added ethyl acetate (150mL×3) to wash, separated by suction filtration, and dried to obtain the product (L-glutamic acid bis-n-butyl hydrochlori...

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Abstract

The invention discloses a butyryl glutamic acid derivative as well as a composition and application thereof. The butyryl glutamic acid derivative disclosed by the invention or a racemic modification,stereisomer, geometric isomer, tautomer and solvate or feed-acceptable salt thereof can be applied in the preparation of novel feed additives and feeds. The invention further discloses a feed composition of the butyryl glutamic acid derivative or the racemic modification, the stereisomer, the geometric isomer, the tautomer and the solvate or the feed-acceptable salt thereof. When applied in animalhusbandry, the butyryl glutamic acid derivative provided by the invention has the effect of improving the production performance of animals, such as increasing animal weight increasing rate, decreasing feed conversion ratio and controlling diarrhea rate, and can be applied as an effective, safe novel feed additive.

Description

Technical field: [0001] The invention belongs to the field of animal feed additives, and in particular relates to a butyryl glutamic acid derivative and a composition containing the butyryl glutamic acid derivative as well as the butyryl glutamic acid derivative and the butyryl glutamic acid derivative Application of the amino acid derivative composition in the preparation of animal feed additives or feed. Background technique: [0002] Feed refers to industrially processed and produced products for animals, and is the main animal food in modern intensive farming. In the process of animal breeding, farmers desire that the feed products eaten by animals can be absorbed and utilized by animals to the maximum extent, so as to improve the production performance of animals so as to achieve the purpose of improving the economic benefits of breeding. Adding feed additives with corresponding functions to feed products can effectively improve the utilization rate of feed products. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/47A23K20/142
CPCA23K20/142C07C233/47
Inventor 彭险峰
Owner GUANGZHOU INSIGHER BIOTECHNOLOGY CO LTD
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