Unlock instant, AI-driven research and patent intelligence for your innovation.

A method for preparing (s)-4-amino-5-mercaptopentanoic acid

A technology of mercaptovaleric acid and amino group, applied in the field of medicine, can solve problems such as cumbersome and trivial matters, and achieve the effects of high yield and short reaction steps

Inactive Publication Date: 2018-05-25
FUDAN UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The preparation method to which it belongs requires a total of 5 steps of reaction, and almost every step needs to be purified by cumbersome column chromatography, but the total yield of the product is only 18%.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for preparing (s)-4-amino-5-mercaptopentanoic acid
  • A method for preparing (s)-4-amino-5-mercaptopentanoic acid
  • A method for preparing (s)-4-amino-5-mercaptopentanoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1 prepares compound GluSH

[0022] Through the following reaction scheme route,

[0023]

[0024] Including the following 3 steps:

[0025] In step 1, the α-carboxyl group is reduced to a primary alcohol starting from an amino- and γ-carboxyl-protected glutamic acid derivative:

[0026] Boc-Glu(OBn)-OH (5.5g) was dissolved in 80mL of anhydrous THF, triethylamine (2.8mL) was added, and ethyl chloroformate (1.75mL ), stirred at -5°C for 30min after dropping, added 20μL of water, and then added sodium borohydride (1.85g, 48.9mmol, 3.0eq) in batches, after the addition was completed, the temperature was naturally raised to 5°C and continued to stir for 1h after no bubbles were generated. When the liquid-mass spectrometry (LC-MS) shows that there is no remaining raw material, add water to quench the reaction, concentrate under reduced pressure, remove most of the solvent, dilute the concentrated solution with ethyl acetate, and then use saturated NaHCO 3 、1M...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of medicine. The invention relates to a simple and convenient preparation method of (S)-4-amino-5-mercaptovaleric acid with potential medical application value. In this method, amino and γ-carboxyl-protected glutamic acid derivatives are used as raw materials, the α-carboxyl group is reduced to primary alcohol, the Mitsunobu reaction is introduced into the sulfhydryl group, and the protecting group is removed to obtain (S)-4-amino-5- Mercaptovaleric acid. Compared with the prior art, the present invention has the advantages of short reaction steps and high yield, only 3 steps are needed, and the total yield is 65.1%.

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 convenient preparation method of (S)-4-amino-5-mercaptopentanoic acid with potential medical application value. Background technique [0002] The prior art discloses that most unnatural amino acids have unique physical and chemical properties compared with natural amino acids, and most of them have been widely used in research in the fields of chemistry, medicine and materials. It is known that 4-amino-5-mercaptopentanoic acid (Glutamate thiol, referred to as GluSH) is a product in which the α-carboxyl group of glutamic acid is replaced by methylene thiol, and is also regarded as a derivative of cysteine. Studies have reported (Wilk, S. et al. Neuropeptides, 1990, 16, 163-168) that GluSH is an inhibitor of glutamyl aminopeptidase (glutamyl aminopeptidase), and has potential application value in the development of...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/58C07C319/06C07C319/02
CPCY02P20/55
Inventor 张伟李英霞吴平
Owner FUDAN UNIV