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A kind of synthetic method of carnosine

A synthesis method and carnosine technology, applied in the field of organic synthesis, can solve the problems of low yield, high cost, long route and the like, and achieve the effects of short synthesis route, reduction of raw material cost, and reduction of environmental pollution

Active Publication Date: 2022-02-15
深圳市迪克曼生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Existing synthetic method, the route that has is long, yield is low, and what have uses expensive reagent (as precious metal catalyst, 3-iodopropionyl chloride) to cause cost height, also has formed explosive intermediate compound and has safe risk

Method used

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  • A kind of synthetic method of carnosine
  • A kind of synthetic method of carnosine
  • A kind of synthetic method of carnosine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Step 1: Add 15g (0.0620mol, 1eq) L-histidine to 10mL tetrahydrofuran and 50mL water at 0-5°C, add 26g (1.5476mol, 5eq) sodium bicarbonate, stir for 30min, slowly add 20g ( 0.3937mol, 2.5eq) 3-chloropropionyl chloride, after the dropwise addition, keep it warm at 0-5°C for 5 hours, follow the complete reaction of L-histidine by TLC, let stand for 30 minutes to separate the phases, and wash the tetrahydrofuran phase with 50mL saturated saline. Dry over anhydrous sodium sulfate, evaporate to dryness under reduced pressure below 50°C to obtain a yellow oil, and obtain 18.5 g (0.0552 mol) g of compound A through column chromatography, with a molar yield of 89%.

[0036] Characterization data: 1 HNMR(400MHz,MeOD):δ8.12(s,1H),6.51(s,1H),4.45-4.49(m,1H),3.76(t,4H),3.31-3.36(dd,2H),2.86( t,4H); 13 CNMR (400MHz, MeOD): 172.3188, 171.5703, 169.5647, 131.9984, 131.5282, 117.3620, 41.0465, 40.7454, 40.3309, 40.1765, 40.0269, 31.2832.

[0037]

[0038] Step 2: Add 1...

Embodiment 2

[0041] Step 1: Add 5kg (32.26mol, 1eq) L-histidine to 1L tetrahydrofuran and 10L water at 0-5°C, add 2.168kg (8eq) sodium bicarbonate, stir for 120min, slowly add 20.48kg (5eq) ) 3-chloropropionyl chloride, after the dropwise addition, keep the reaction at 0-5°C for 10 hours, TLC traces the complete reaction of L-histidine, let it stand for 60 minutes to separate the phases, wash the tetrahydrofuran phase with 5L saturated saline, and dry over anhydrous sodium sulfate , Evaporated to dryness under reduced pressure below 50°C to obtain Compound A as a yellow oil.

[0042] The second step: Add the compound A obtained in the first step into the high-pressure reactor, add 95L of 20wt% ammonia water, vacuumize and fill the ammonia gas to 0.5MPa, heat to 60°C, keep the temperature for 18 hours, TLC traces the complete reaction of the raw materials , extract excess ammonia gas, evaporate the solvent to obtain the crude product, add 1L deionized water and 5L ethanol, precipitate a whi...

Embodiment 3

[0045] Step 1: Add 3mol (1eq) L-histidine to 500mL tetrahydrofuran and 1L water at 0-5°C, add 9mol (3eq) sodium carbonate, stir for 60min, slowly add 6mol (2eq) 3-chloropropionyl chloride dropwise After the dropwise addition, keep it warm at 0-5°C for 8 hours, track the complete reaction of L-histidine by TLC, let it stand for 30 minutes to separate the phases, wash the tetrahydrofuran phase with 1L saturated brine, dry over anhydrous sodium sulfate, and reduce pressure below 50°C Evaporate to dryness to obtain Compound A as a yellow oil.

[0046] The second step: Add the compound A obtained in the first step into a high-pressure reactor, add 6L of 20wt% ammonia water, vacuumize and fill with ammonia gas to 0.4MPa, heat to 80°C, keep the temperature for 14 hours, TLC traces the reaction of the raw materials completely , extract excess ammonia gas, evaporate the solvent to obtain the crude product, add 200mL deionized water and 800mL ethanol, precipitate a white solid, obtain 5...

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Abstract

The invention belongs to the field of organic synthesis, and discloses a synthesis method of carnosine, comprising the following steps: S1, reacting histidine with 3-chloropropionyl chloride to obtain compound A; S2, ammoniating compound A; the present invention uses an organic solvent ‑Water two-phase reaction solves the problem that histidine is difficult to dissolve in organic solvents, and avoids the decomposition of 3‑chloropropionyl chloride in water at the same time, the synthetic route is shorter, the cost of reagents and raw materials used is low, the reaction conditions are mild, and the comprehensive yield high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing carnosine. Background technique [0002] Carnosine is a natural dipeptide composed of β-alanine and histidine, which naturally exists in various tissues of the body, especially in muscle and brain tissues. Carnosine is mainly synthesized by carnosine synthase in skeletal muscle, cardiac muscle and certain brain regions. In 1900, Russian scholars Glewitsch and Amirad zhibi discovered it for the first time in the skeletal muscles of vertebrates, and studied its physical and chemical properties. In recent years, people have begun to study its physiological functions. [0003] Carnosine has a wide range of functions, such as anti-oxidation, metal ion chelation, acid-base buffering, inhibition of telomere shortening, inhibition of mitochondrial damage, anti-glycosylation, anti-tumor and other effects. Animal experiments have found that carnosine can play a ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 杨超文王蕾符定良宋家良关志帅
Owner 深圳市迪克曼生物科技有限公司
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