Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of novel non-natural antioxidation peptide

An antioxidant peptide, non-natural technology, applied in the field of biomedicine, can solve the problems of blindness and separation difficulties of active peptides

Active Publication Date: 2019-03-08
ZHEJIANG OCEAN UNIV
View PDF5 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a preparation method of a novel non-natural antioxidant peptide, reacting taurine with clam tripeptide Trp-Pro-Pro to obtain a novel polypeptide with enhanced antioxidant activity or anticancer activity, and the synthesis process of the polypeptide Amino deprotection agent and peptide synthesis accelerator are used in the process to achieve the purpose of complete amino deprotection and high purity of peptide synthesis; at the same time, it solves the shortcomings of blindness and difficult separation in the process of preparing active peptides only by enzymatic protein hydrolysis, and has a wide range of applications prospect

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
  • Preparation method of novel non-natural antioxidation peptide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Synthetic structure is the tripeptide of Tau-Trp-Pro, comprises the following steps:

[0074] S1. Mix Fmoc-Pro(Boc)-OH and Wang Resin in proportion, add HOBT and DIC activators, use DMF as solvent, shake and react at 43°C for 2.5h, and the reaction product is obtained after filtering, washing with DMF and ethanol Fmoc-Pro(Boc)-Wang Resin; wherein, the number of moles of Fmoc-Pro(Boc)-OH is 2.2 times that of the resin; the number of moles of the activator is 3.4 times that of the resin;

[0075] S2. With the Fmoc-Pro(Boc)-Wang Resin obtained in step S1, the Fmoc group is removed to obtain H-Pro(Boc)-Wang Resin (take the resin and use ninhydrin chromogenic agent for color inspection, the color is dark blue or blue-purple , it shows that the Fmoc group has been removed); then add Fmoc-Trp(Trt)-OH, then add (S)-(+)-3-(1-naphthyloxy)-1-phenyl-1-propanol and Ethylene glycol monophenyl ether was reacted at 30°C for 45 minutes to obtain Fmoc-Trp(Trt)-Pro(Boc)-Wang Resin;

[0...

Embodiment 2

[0081] Synthetic structure is the tripeptide of Trp-Tau-Pro, comprises the following steps:

[0082] S1. Mix Fmoc-Pro(Boc)-OH and Wang Resin in proportion, add HOBT and HBTU activators, and use DMF as solvent to shake and react at 43°C for 2.5h. The reaction product is filtered, DMF and Obtain Fmoc-Pro(Boc)-Wang Resin after ethanol washing; Wherein, the number of moles of Fmoc-Pro(Boc)-OH is 2.2 times of resin; The number of moles of activator is 3.4 times of resin;

[0083] S2. With the Fmoc-Pro(Boc)-Wang Resin obtained in step S1, the Fmoc group is removed to obtain H-Pro(Boc)-Wang Resin (take the resin and use ninhydrin chromogenic agent for color inspection, the color is dark blue or blue-purple , indicating that the Fmoc group has been removed); then add Fmoc-Tau-OH, then add (S)-(+)-3-(1-naphthyloxy)-1-phenyl-1-propanol and ethylene glycol Monophenyl ether was reacted at 30°C for 45 minutes to obtain Fmoc-Tau-Pro(Boc)-Wang Resin;

[0084] S3. With the Fmoc-Tau-Pro(Boc)...

Embodiment 3

[0089] The synthetic structure is the tetrapeptide of Tau-Trp-Pro-Pro, comprises the following steps:

[0090] S1. Mix Fmoc-Pro(Boc)-OH and Wang Resin in proportion, add HOBT and HBTU activators, and use DMF as solvent to shake and react at 43°C for 2.5h. The reaction product is filtered, DMF and Obtain Fmoc-Pro(Boc)-Wang Resin after ethanol washing; Wherein, the number of moles of Fmoc-Pro(Boc)-OH is 2.2 times of resin; The number of moles of activator is 3.4 times of resin;

[0091] S2. With the Fmoc-Pro(Boc)-Wang Resin obtained in step S1, the Fmoc group is removed to obtain H-Pro(Boc)-Wang Resin (take the resin and use ninhydrin chromogenic agent for color inspection, the color is dark blue or blue-purple , indicating that the Fmoc group has been removed); then add Fmoc-Pro(Trt)-OH, then add (S)-(+)-3-(1-naphthyloxy)-1-phenyl-1-propanol and Ethylene glycol monophenyl ether was reacted at 30°C for 45 minutes to obtain Fmoc-Pro(Trt)-Pro(Boc)-Wang Resin;

[0092] S3. Remove...

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 provides a preparation method of a novel non-natural antioxidation peptide and belongs to the field of biological medicine. The synthesis method of the novel polypeptide comprises the steps of performing resin grafting reaction on Fmoc-Pro(Boc)-OH, and then performing coupled reaction with Pro or Trp amino acid and taurine to form the novel polypeptide such as Tau-Trp-Pro, Trp-Tau-Pro, Tau-Trp-Pro-Pro, Trp-Pro-Tau-Pro and Trp-Tau-Pro-Pro, wherein a Fmoc removal group adopts a deprotection agent combination: piperidine, potassium tert-butoxide and HOBT in a reaction process. Taurine reacts with a tegillarca granosa tripeptide Trp-Pro-Pro to form the novel polypeptide with improved antioxidation activity or anticancer activity; in a synthesis process of the polypeptide, amino deprotection is complete; and the synthesis purity of the polypeptide is high.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a preparation method of a novel non-natural antioxidant peptide. Background technique [0002] Taurine is a sulfur-containing non-protein amino acid, which has a wide range of physiological activities and can regulate the normal physiological activities of the body, such as promoting the brain tissue and intellectual development of infants and young children, and enhancing the antioxidant capacity of cells. The distribution of taurine is very extensive, and marine organisms, such as sea fish, shellfish, such as cuttlefish, octopus, shrimp, oyster, conch, clam, etc. are rich in taurine. Taurine exists in a free form in organisms and does not participate in protein synthesis. By chemical synthesis, taurine can be reacted with other amino acids to form a new type of non-natural peptide, which can endow the biological activity that the natural protein peptide does not have. T...

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 Applications(China)
IPC IPC(8): C07K5/078C07K5/097C07K1/06C07K1/04C07D403/12A61P39/06
CPCA61P39/06C07D403/12C07K5/06156C07K5/06165C07K5/0821
Inventor 金火喜徐红萍梁建灏尹啸杨立业
Owner ZHEJIANG OCEAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com