Cyclopeptide compound GG6F and preparation method thereof

A compound and cyclic hexapeptide technology, applied in the field of cyclic hexapeptide compound GG6F and its chemical preparation, can solve problems such as cyclic hexapeptide compounds that have not yet been seen, and achieve the effects of high yield and simple preparation equipment steps

Inactive Publication Date: 2015-08-26
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In recent years, the use of new organic condensing agents for azabenzoxazoles, including HATU, TBTU and HBTU, has provided great help for the study of peptide synthesis methods; Reports on chemical preparation methods

Method used

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  • Cyclopeptide compound GG6F and preparation method thereof
  • Cyclopeptide compound GG6F and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 chemically prepares GG6F

[0024] The chemical preparation methods include solid-phase synthesis of linear peptides, liquid-phase ring closure, extraction and column chromatography;

[0025] 1. Synthesis of GG6F linear precursor

[0026] (1) Take the resin: weigh a certain amount of Fmoc-Gly-Wang resin, and swell it in DMF for 15 minutes;

[0027] (2) Remove the Fmoc protecting group: Stir and react with nitrogen in 20% piperidine / DMF solution for 30 minutes; then wash with equal volume of DMF repeatedly for 3 times, each time for 3 minutes;

[0028] (3) Ninhydrin detection: Take a small amount of the reacted resin in a test tube, add 2 drops of 1% (volume fraction, the same below) ninhydrin / ethanol solution, heat for about 2 minutes; the resin is blue-purple or purple-red, It means that the deprotection is successful, proceed to the next step of the reaction; if the resin does not change color, it means that the deprotection is not successful, repeat the...

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Abstract

The present invention belongs to the pharmaceutical field, and relates to a cyclic hexapeptide compound GG6F having a structure represented by a formula (I), and a chemical preparation method thereof, wherein six alpha-L-amino acids are sequentially bound in a head-to-tail manner to form the cyclic hexapeptide compound GG6F, and the cyclic hexapeptide compound GG6F is represented by cyclo-(Gly-Leu-Val-Leu-Leu-Phe). According to the present invention, the Wang resin is adopted as a solid phase support, HATU / HOAt is adopted as a condensing agent, N,N-dimethylformamide is adopted as a solvent, a linear peptide precursor is subjected to solid-phase synthesis, the cyclopeptide is chemically prepared through liquid phase ring closing, the reaction product GG6F is purified through column chromatography, and the structure is confirmed through NMR spectroscopy and mass spectrometry. The preparation method of the present invention has characteristics of simple step and high yield, and is suitable for preparing the pharmaceutically active cyclic hexapeptide. The formula (I) is defined in the instruction.

Description

technical field [0001] The invention belongs to the field of chemistry, and relates to a peptide compound and a chemical preparation method thereof, in particular to a cyclic hexapeptide compound GG6F and a chemical preparation method thereof. Background technique [0002] The prior art discloses that cyclic peptide components have a high structural similarity with ordinary (linear) peptides in composition and structure, but cyclic peptide compounds are different from linear peptide structures because of the amino acid residues in the main structure connected to form a ring. different, so that the drug properties are different: first, the free carboxyl and amino groups in the cyclic peptide compound molecule disappear, so that its water solubility is significantly reduced, the polarity in the solvent is reduced, and the fat solubility of the compound is enhanced; Two, the disappearance of free amino and carboxyl groups makes the sensitivity of the cyclic peptide compound to ...

Claims

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Application Information

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IPC IPC(8): C07K7/64C07K1/16C07K1/06C07K1/04C07K1/02
Inventor 陈杰桃丁慧文穆青杨萍
Owner FUDAN UNIV
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