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Synthesizing method of N-beta-alanyl-(tau-methyl) histidine

A synthetic method and technology of histidine, applied in the direction of organic chemistry, etc., can solve problems such as methylation

Inactive Publication Date: 2010-11-24
GL BIOCHEM SHANGHAI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of synthetic method of N-beta-alanyl-(τ-methyl) histidine, mainly solves when conventional method carries out methylation to the τ position of histidine, often will Technical issues with methylation at the π position

Method used

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  • Synthesizing method of N-beta-alanyl-(tau-methyl) histidine
  • Synthesizing method of N-beta-alanyl-(tau-methyl) histidine
  • Synthesizing method of N-beta-alanyl-(tau-methyl) histidine

Examples

Experimental program
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Embodiment 1

[0021] (1) Preparation of N-benzyloxycarbonyl-β-alanine

[0022] Add 750ml of water, 150 grams (1.685mol) of β-alanine, 212 grams (2.527mol) of sodium bicarbonate and 440 grams of benzyloxycarbonyl succinimide in a beaker, and use 2mol / L sodium hydroxide solution Control the pH value between 8 and 9, extract impurities with ether after the reaction is complete, and discard the ether phase. The aqueous phase was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to remove most of the ethyl acetate, frozen overnight, filtered to obtain 208 g of white crystals, yield: 55.3%.

[0023] (2) Preparation of histidine methyl ester hydrochloride

[0024] Add 6.5L of anhydrous methanol to a 10L three-necked flask, add 620 grams (4mol) of L-histidine, and dropwise add 855ml (12mol) of thionyl chloride. After the reaction is completed, directly transfer it to a 20L clean container, add 5L ether, filter 940 g of white crystals were o...

Embodiment 2

[0040] (1) Preparation of N-benzyloxycarbonyl-β-alanine

[0041] Add 750ml of water, 150 grams (1.685mol) of β-alanine, 212 grams (2.527mol) of sodium bicarbonate and 440 grams of benzyloxycarbonyl succinimide in a beaker, and use 2mol / L sodium hydroxide solution Control the pH value between 8 and 9, extract impurities with ether after the reaction is complete, and discard the ether phase. The aqueous phase was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to remove most of the ethyl acetate, frozen overnight, filtered to obtain 208 g of white crystals, yield: 55.3%.

[0042] (2) Preparation of histidine methyl ester hydrochloride

[0043] Add 6.5L of anhydrous methanol to a 10L three-necked flask, add 620 grams (4mol) of L-histidine, and dropwise add 855ml (12mol) of thionyl chloride. After the reaction is completed, directly transfer it to a 20L clean container, add 5L ether, filter 940 g of white crystals were o...

Embodiment 3

[0059] (1) Preparation of N-benzyloxycarbonyl-β-alanine

[0060] Add 750ml of water, 150 grams (1.685mol) of β-alanine, 212 grams (2.527mol) of sodium bicarbonate and 440 grams of benzyloxycarbonyl succinimide in a beaker, and use 2mol / L sodium hydroxide solution Control the pH value between 8 and 9, extract impurities with ether after the reaction is complete, and discard the ether phase. The aqueous phase was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to remove most of the ethyl acetate, frozen overnight, filtered to obtain 208 g of white crystals, yield: 55.3%.

[0061] (2) Preparation of histidine methyl ester hydrochloride

[0062] Add 6.5L of anhydrous methanol to a 10L three-necked flask, add 620 grams (4mol) of L-histidine, and dropwise add 855ml (12mol) of thionyl chloride. After the reaction is completed, directly transfer it to a 20L clean container, add 5L ether, filter 940 g of white crystals were o...

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Abstract

The invention discloses a synthesizing method of N-beta-alanyl-(tau-methyl) histidine, which solves the technical problem that the bit tau is usually methylated when the bit tau of the histidine is methylated by the regular method. The synthesizing method comprises the following steps of using L-histidine and methanol under the action of thionyl chloride to generate L-histidine methyl ester hydrochloride, reacting with carbonyl diimidazole to generate L-histidine methyl ester comround, reacting with methylating reagent to generate quaternary ammonium of the L-histidine methyl ester comround, performing acid hydrolysis on the quaternary ammonium to obtain L-(tau-methyl) histidine, then performing methylation to obtain L-(tau-methyl) histidine methyl ester hydrochloride, coupling with beta-alanine protected by benzoyloxycarbonyl group to obtain Z-beta-Ala-His(tau-Me)-OMe, hydrolyzing the methyl ester and hydrogenating protection of the benzoyloxycarbonyl group to obtain the final output of N-beta-alanyl-(tau-methyl) histidine. The synthesizing method prevents the hydrogen atom during side reaction from migrating from the bit tau to the bit pi.

Description

technical field [0001] The present invention relates to the synthesis method of N-beta-alanyl-(τ-methyl)histidine. Background technique [0002] Carnosine is a dipeptide (β-Ala-His-OH) composed of β-alanine and L-histidine, which widely exists in various organs and tissues of the body, especially in muscles, brains and eye lenses. Up to 20mmol / L. Carnosine related compounds (CRCs), such as N-β-alanyl-(τ-methyl) histidine, anserine, acetylcarnosine and homocarnosine, etc., they Can be transformed into each other to meet physiological needs. Carnosine and carnosine analogs are another series of natural non-enzymatic free radical scavengers and antioxidants discovered after SOD and vitamin E. The complexes formed by combining them with copper and zinc can have the same effect as SOD. Carnosine and its The analogue can inhibit fat oxidation catalyzed by metal ions, hemoglobin, esterase and active oxygen, does not affect the texture of food, and can be used in food as a natura...

Claims

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Application Information

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IPC IPC(8): C07D233/64
Inventor 奚文波周志国王卫国徐红岩
Owner GL BIOCHEM SHANGHAI
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