Novel method for synthesizing L-carnosine

Abstract

The invention discloses a synthesis method for L-Carnosine. In the prior art, the imidazole ring of the L-Histidine can take part in the reaction and has side-reactions, which decreases the yields of the products and makes the L-Carnosine assume the toxicity at the same time. In this invention, the o-phthalic anhydride is reacted with beta-alanine to produce the o-phthalic beta-alanine, the o-phthalic beta-alanine is made an acyl chlorination by the chloro-substitution reagent to synthesize into the o-phthalic beta-alanyl chloride; L-Carnosine is reacted with the edittrialkyl chlorosilane or hexamethyldisilazane to produce the trialky silane protection compound which is condensed with the o-phthalic beta-alanyl chloride to produce the hydrochloride; the hydrochloride is made a de-protection by the absolute alcohol, and then is neutralized by the basic solution to produce a product of neutralization; the hydrazine hydrate is used for a hydrazinolysis to the product of neutralization, then the L-Carnosine is precipitated from the absolute alcohol. The invention protects the imidazole ring on the L-Carnosine, avoids that the imidazole ring on the L-Carnosine makes side-reactions with other substances so as to obtain the pure L-Histidine, has low side-effects and high total yields as well as contents.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a new synthesis method of L-carnosine. Background technique [0002] Carnosine is a small molecule of natural dipeptide left-handed structure ubiquitous in nature. It is a dipeptide composed of β-alanine and L-histidine. Carnosine has cell anti-oxidation, anti-aging properties and a variety of physiological health care functions and medical effects. It has therapeutic effects on hypertension, heart disease, senile cataract, ulcer healing, etc. Exciting factors and other effects. There is a common shortcoming in the multiple methods of synthesizing carnosine at present: due to being restricted by the side reaction, this side reaction is to carry out under the participation of the imidazole ring of L-histidine, and L-histidine has at least Racemization will occur above 0.8%, which reduces the yield of the product; it is difficult to separate the L-carnosine with good optical puri...

AI Technical Summary

Problems solved by technology

There is a common shortcoming in the multiple methods of synthesizing carnosine at present: due to being restricted by the side reaction, this side reaction is to carry out under the participation of the imidazole ring of L-histidine, and L-histidine has at least Racemization will occur above 0.8%, which reduces the yield of the product; it is difficult to separate the L-carnosine with good optical purity from the toxic mixture (their racemic form, imidazole isomers, etc.) simultaneously, Product purity is affected due to the similar physicochemical properties of these compounds to L-carnosine

Synthetic L-carnosine exhibits toxicity due to the presence of these mixtures, rather than the original pure preparation

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