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cyclopeptide cyclo-[(asn) 5 -cys] preparation method

A 5-cys and cyclic peptide technology, which is applied in the field of homocyclic peptide compound Cyclo-[5-Cys] and its synthesis and preparation, to achieve the effects of simple operation, reasonable process and high synthesis efficiency

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]. 2013-11-15.), there is no related new cyclic peptide Cyclo-[(Asn) 5 -Cys], especially the reports on its chemical preparation methods

Method used

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  • cyclopeptide cyclo-[(asn) <sub>5</sub> -cys] preparation method
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  • cyclopeptide cyclo-[(asn) <sub>5</sub> -cys] preparation method

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Embodiment 1

[0027] A homocyclic peptide Cyclo-[(Asn) 5 -Cys] preparation method, comprising:

[0028]Step 1. Soak the 2-chlorotrityl chloride resin in dichloromethane, shake for 30 minutes, remove the solvent after swelling and suction filtration, and take the fluorenyl moxycarbonyl protecting group in the amino group and the trityl protecting group in the amido group. Add a three-fold molar excess of paraparagine and a ten-fold molar excess of N,N-diisopropylethylamine to the resin, then add as little DMF as possible to dissolve it, and shake it at room temperature for 30 minutes; then add methanol and incubate for 20 minutes to seal off the resin Reactive sites on the resin; 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 a DMF solution containing 20% ​​piperidine by volume, soak for 5min, and reciprocate for about 4 times, remove the protecting group fluorenyl moxycarbonyl o...

Embodiment 2

[0033] A homocyclic peptide Cyclo-[(Asn) 5 -Cys] preparation method, comprising:

[0034] Step 1. Soak the 2-chlorotrityl chloride resin in dichloromethane, shake for 30 minutes, remove the solvent after swelling and suction filtration, and take the fluorenyl moxycarbonyl protecting group in the amino group and the trityl protecting group in the amido group. Add a three-fold molar excess of paraparagine and a ten-fold molar excess of N,N-diisopropylethylamine to the resin, then add as little DMF as possible to dissolve it, and shake it at room temperature for 30 minutes; then add methanol and incubate for 20 minutes to seal off the resin Reactive sites on the resin; 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 a DMF solution containing 20% ​​piperidine by volume, soak for 5min, and reciprocate for about 4 times, remove the protecting group fluorenyl moxycarbonyl ...

Embodiment 3

[0039] A homocyclic peptide Cyclo-[(Asn) 5 -Cys] preparation method, comprising:

[0040] Step 1. Soak the 2-chlorotrityl chloride resin in dichloromethane, shake for 30 minutes, remove the solvent after swelling and suction filtration, and take the fluorenyl moxycarbonyl protecting group in the amino group and the trityl protecting group in the amido group. Add a three-fold molar excess of paraparagine and a ten-fold molar excess of N,N-diisopropylethylamine to the resin, then add as little DMF as possible to dissolve it, and shake it at room temperature for 30 minutes; then add methanol and incubate for 20 minutes to seal off the resin Reactive sites on the resin; 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 a DMF solution containing 20% ​​piperidine by volume, soak for 5min, and reciprocate for about 4 times, remove the protecting group fluorenyl moxycarbonyl ...

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Abstract

The invention discloses a preparation method of homocyclic peptide Cyclo-[(Asn)5-Cys]. The method includes: (1) connection of resin with protective group equipped asparagine to form asparagine connected resin; (2) sequential condensation of the asparagine connected to resin with the protective group equipped asparagine and cysteine 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-[(Asn)5-Cys] provided by the invention is a homocyclic peptide structure, has a similar structure to crown ether compounds, and compared with the heterocyclic peptide, has better regularity in terms of molecule structure, 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 amino functional groups contained on a side chain endow the product with certain water solubility and bioactivity, and a mercapto 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.

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 cyclopeptide compound Cyclo-[(Asn) 5 -Cys] and its synthetic preparation method. 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 significantly improved. [0003]...

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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