Preparation method of homocyclic peptide 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 good regularity, simple operation 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

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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 gr

Method used

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  • Preparation method of homocyclic peptide Cyclo-[(Asp)5-Gly]
  • Preparation method of homocyclic peptide Cyclo-[(Asp)5-Gly]

Examples

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Example Embodiment

[0027] Example 1:

[0028] A homocyclic peptide Cyclo-[(Asp) 5- The preparation method of Gly] includes:

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

Example Embodiment

[0033] Example 2:

[0034] A homocyclic peptide Cyclo-[(Asp) 5- The preparation method of Gly] includes:

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

Example Embodiment

[0039] Example 3:

[0040] A homocyclic peptide Cyclo-[(Asp) 5- The preparation method of Gly] includes:

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

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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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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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