Preparation method of homocyclic peptide Cyclo-[(Asn)5-Cys]

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: 2017-11-28
INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology describes how certain cyclodepsipeptides can form stable structures called cocycles when combined together through chemical bonds between their atoms (their rings). These complex structures make them easy to assemble into various types of nanoelectronic devices such as transistors, sensing elements, batteries, fuel cells, and other electronic components like switches. They provide improved performance compared to traditional methods due to more precise control over specific properties.

Problems solved by technology

This patented technical describes different ways to make certain types of compounds called cyclodepsipeptides that can be easily obtained from natural sources like proteins without losing their original function due to decomposition during manufacturing processes such as purification steps. However, these techniques require complicated procedures involving multiple stages which slow down production times and increase costs associated with each stage. Therefore, this patents proposes an alternative approach where cyclodystroplexes formed through linking together rings rather than just connecting ends may improve efficiency and reduce cost compared to traditional approaches.

Method used

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  • Preparation method of homocyclic peptide Cyclo-[(Asn)5-Cys]

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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

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Claims

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Application Information

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Owner INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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