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(S)-4-amino-5-mercaptopentanoic acid preparation method

A technology of mercaptovaleric acid and amino, which is applied in the field of medicine, can solve cumbersome problems, and achieve the effects of simple washing operation, high yield and easy purification

Inactive Publication Date: 2016-12-07
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In this method, 5 steps of reaction are required, and after almost every step of reaction, cumbersome column chromatography purification is required, and the total yield is only 18%.

Method used

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Embodiment 1

[0025] Example 1 Preparation of GluSH

[0026] Through the following reaction route:

[0027]

[0028] Follow the steps below:

[0029] In the first step, D-cysteine ​​with protected sulfhydryl and amino groups is condensed with Michaelis acid to generate β-ketoester:

[0030] Boc-S-trityl-D-cysteine ​​(5.00 g) and Michaelis acid (1.71 g) were dissolved in 100 mL of dry dichloromethane in turn, and 4-dimethylaminopyridine ( 1.98g), after stirring in an ice bath for 10min, dicyclohexylcarbodiimide (2.45g) was added, and after stirring for 8h under ice bath conditions, liquid mass spectrometry (LC-MS) and thin layer chromatography (TLC) showed that the reaction complete, add saturated ammonium chloride to quench the reaction, and wash with 1M hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride successively, dry over anhydrous sodium sulfate, concentrate under reduced pressure to obtain a light brown powdery solid, wash twice with ether Finally, 5....

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Abstract

The present invention belongs to the technical field of medicine, and relates to a preparation method of (S)-4-amino-5-mercaptopentanoic acid having potential medical application value. According to the method of the present invention, amino-protected and mercapto-protected D-cysteine is adopted as a raw material and is subjected to condensation with Meldrum's acid to generate beta-ketone ester, the ketone carbonyl is subjected to reducing elimination, lactam is formed through decarboxylation, the protection groups on mercapto and amino are removed, and the lactam ring is opened to prepare the (S)-4-amino-5-mercaptopentanoic acid. According to the present invention, the method has following advantages that reaction steps are short, wherein only the four steps are required; the purification is easy, wherein only the simple washing operation is required; and the yield is high, wherein the total yield of the four steps is 76.0%.

Description

technical field [0001] The invention belongs to the technical field of medicine. The invention relates to a preparation method of an amino acid, in particular to a preparation method of (S)-4-amino-5-mercaptovaleric acid with potential medical application value. Background technique [0002] According to research reports, compared with natural amino acids, most unnatural amino acids have unique physical and chemical properties, and have been widely used in the research of chemistry, medicine and materials. 4-Amino-5-mercaptopentanoic acid (Glutamate thiol, abbreviated as GluSH) is a product in which the α-carboxyl group of glutamic acid is replaced by a methylene thiol group, and can also be regarded as a derivative of cysteine. Literature (Wilk, S. et al. Neuropeptides, 1990, 16, 163-168) reported that GluSH is an inhibitor of glutamyl aminopeptidase (glutamyl aminopeptidase), and has potential application value in the research and development of antihypertensive drugs (Cl...

Claims

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Application Information

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IPC IPC(8): C07C323/58C07C319/06
CPCY02P20/55
Inventor 张伟李英霞吴平
Owner FUDAN UNIV
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