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Preparation method of cyclopeptide cyclo-[(asp)5-gly]

A cyclic peptide and resin technology is applied in the field of cyclic peptide compound Cyclo-[5-Gly] and its synthesis and preparation, and achieves the effects of high synthesis efficiency, simple operation and good regularity

Active Publication Date: 2020-07-21
INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In recent years, 2-(7-azobenzotriazole)-tetramethyluronium hexafluorophosphate (HATU), benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate Fluorophosphate (HBTU), 1-hydroxybenzotriazole (HOBt), O-benzotriazole-N,N,N',N'-tetramethyluronium tetrafluoroboric acid (TBTU) and other benzo The use of azole organic condensing agents has provided great help for the research on cyclic peptide synthesis methods; but so far, it has been mainly used in the synthesis of RGD cyclic peptides (cyclic peptides containing arginine-glycine-aspartic acid) ( Wang Xiping. RGD synthesis and preparation process. CN, 103588863B[P]. 5 -Gly], especially the report on the related process of its chemical preparation method

Method used

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  • Preparation method of cyclopeptide cyclo-[(asp)5-gly]
  • Preparation method of cyclopeptide cyclo-[(asp)5-gly]
  • Preparation method of cyclopeptide cyclo-[(asp)5-gly]

Examples

Experimental program
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Effect test

Embodiment 1

[0028] A homocyclic peptide Cyclo-[(Asp) 5- Gly] preparation method, comprising:

[0029] Step 1. Soak the 2-chlorotrityl chloride resin in dichloromethane and shake it for 30 minutes; remove the solvent after the resin is swollen, and take the amino group with fluorenyl moxycarbonyl protection group and the terminal carboxyl group with tert-butyl ester protection group. Add a three-fold molar excess of aspartic acid and a ten-fold molar excess of N,N-diisopropylethylamine to the resin, then add DMF to dissolve them, shake and react at room temperature for 30 minutes; then add methanol and incubate for 20 minutes; seal off the resin The active site of the reaction; wash the resin repeatedly with DMF and methanol solvent and remove the solvent, the first amino acid is connected to the resin; after removing the solvent, add the lysate to remove the protecting group fluorenylmethoxycarbonyl on the amino group of aspartic acid Acyl group: Take a few resins, wash them thoroughly w...

Embodiment 2

[0034] A homocyclic peptide Cyclo-[(Asp) 5- Gly] preparation method, comprising:

[0035] Step 1. Soak the 2-chlorotrityl chloride resin in dichloromethane and shake it for 30 minutes; remove the solvent after the resin is swollen, and take the amino group with fluorenyl moxycarbonyl protection group and the terminal carboxyl group with tert-butyl ester protection group. Add a three-fold molar excess of aspartic acid and a ten-fold molar excess of N,N-diisopropylethylamine to the resin, then add DMF to dissolve it, and shake it at room temperature for 60 minutes; then add methanol and incubate for 20 minutes; use DMF and methanol The solvent repeatedly washes the resin and removes the solvent, and the first amino acid is connected to the resin; after removing the solvent, add the lysate to remove the protecting group fluorenyl moxycarbonyl on the amino group of aspartic acid; After cleaning, add one drop each of 5% ninhydrin ethanol solution, 0.3% ascorbic acid solution, and ...

Embodiment 3

[0040] A homocyclic peptide Cyclo-[(Asp) 5- Gly] preparation method, comprising:

[0041] Step 1. Soak the 2-chlorotrityl chloride resin in dichloromethane and shake it for 30 minutes; remove the solvent after the resin is swollen, and take the amino group with fluorenyl moxycarbonyl protection group and the terminal carboxyl group with tert-butyl ester protection group. Add a three-fold molar excess of aspartic acid and a ten-fold molar excess of N,N-diisopropylethylamine to the resin, then add DMF to dissolve it, and shake it at room temperature for 30 minutes; then add methanol and incubate for 20 minutes; use DMF and methanol The solvent repeatedly washes the resin and removes the solvent, and the first amino acid is connected to the resin; after removing the solvent, add the lysate to remove the protecting group fluorenyl moxycarbonyl on the amino group of aspartic acid; After cleaning, add one drop each of 5% ninhydrin ethanol solution, 0.3% ascorbic acid solution, and ...

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Abstract

The invention discloses a preparation method of homocyclic peptide Cyclo-[(Asp)5-Gly]. The method includes: (1) connection of resin with protective group equipped aspartic acid to form aspartic acid connected resin; (2) sequential condensation of the aspartic acid connected to resin with the protective group equipped aspartic acid and allylglycine to form linear peptide connected resin; (3) cutting of the linear peptide off the resin and end-to-end cyclization to obtain a cyclic peptide crude product; and (4) purification and preservation of cyclic peptide. The Cyclo-[(Asp)5-Gly] prepared by the invention is a homocyclic peptide structure, has a molecular structure with better regularity, is easier for self-assembly into an ion channel or nanotube, thus serving as a drug carrier, membrane channel, molecular device and the like. The five carboxyl functional groups contained on a side chain endow the product with certain water solubility and bioactivity, also an allyl functional group contained on the side chain endows the product with better reaction activity, so that the product can be used as a precursor reagent for high efficient click reaction. At the same time, the method has the advantages of reasonable process, simple operation, and high synthesis efficiency.

Description

technical field [0001] The invention belongs to the technical field of polypeptide synthesis, and relates to a chemical preparation method of cyclic peptide compounds, in particular to the cyclic peptide compound cyclic peptide Cyclo-[(Asp) 5 -Gly] and its synthesis preparation process. Background technique [0002] Cyclic peptides have a high structural similarity with ordinary chain peptides in terms of structural composition, but because the amino acid residues in the main structure participate in the connection to form a ring, the free carboxyl, amino and other hydrophilic groups in the molecule disappear or decrease. It reduces its polarity, enhances its fat solubility, reduces its sensitivity to ammonia / carboxypeptidase in vivo, and increases its stability in vivo; at the same time, the degree of freedom of peptide chain movement decreases, and it has a relatively stable and definite conformation in solution. The probability of fitting with the receptor is significant...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/64C07K1/06C07K1/04
CPCC07K7/64Y02P20/55
Inventor 宋宏涛
Owner INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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