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Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof

An immunosuppressant, synthetic technology, applied in the fields of peptides, organic chemistry, drug combination, etc., can solve the problems of difficult chemical synthesis and unfavorable purification, and achieve the effects of stable physical and chemical properties, high yield and high purity

Active Publication Date: 2008-10-22
CHINESE PEPTIDE CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The amino acid residues in the natural structure of HS-1 are all hydrophobic amino acids, and the sequence is rich in Pro with a secondary amine ring structure, which makes chemical synthesis extremely difficult and is also very unfavorable for purification

Method used

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  • Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof
  • Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof
  • Cyclic peptide with -val-sta-leu- residue segment and used as immunity inhibitor and synthetic process thereof

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Experimental program
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Embodiment Construction

[0028] The technical solutions of the present invention will be further specifically described below through examples.

[0029] 1 synthetic part

[0030] 1.1 Instruments and reagents

[0031] Peptide synthesizer (ABI 433, American ABI company), semi-preparative high performance liquid chromatography (WatersDelta Prep 4000, American Waters company), analytical high performance liquid chromatography (Agilent 1100, American Agilent company), freeze dryer ( ChristAlpha, German CHRIST company), ion trap mass spectrometer (LCQ Deca, American Thermo-Finnigan company), ultraviolet spectrophotometer (BeckmanDU7400, American Beckman company), C18 reversed-phase analysis column (Waters XTerra, 3.5um, 4.6×150mm).

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Abstract

The invention relates to a cyclic peptide which is provided with a residue fragment of -Val-Sta-Leu- and is used as immunosuppressive agents, and the synthesis process of the cyclic peptide (Ile-Ile-Pro-Pro-Tyr-Val-Sta-Leu) consists of 1) removing amino-protecting groups, 2) transpeptidase reaction, 3) the cutting of a peptide chain, 4) cyclization of the peptide chain. The cyclic peptide compounds which are provided with the residue fragment of Val-Sta-Leu- and used as immunosuppressive agents and have a high yield and a high purity can be obtained, and the immunosuppressive activity of the cyclic peptide compounds is higher. Through the experiments of the retarding effect of A3HS1 towards the delayed hypersensitivity of mice, the influence of phagocytic function of macrophages, and the retarding effect of the proliferation of lymphocytes, the A3HS1 shows a stronger immunosuppressive effect than HS-1, which reaches or surpasses the immunosuppressive of the positive contrast (cyclosporine).

Description

technical field [0001] The invention relates to a peptide compound, specifically a cyclic peptide with a -Val-Sta-Leu- residue fragment that can be used as an immunosuppressant and a synthesis process. Background technique [0002] Hymenistatin-1 (HS-1) is a cyclic octapeptide isolated from the Pacific hymeniacidon sponge by researchers such as Pettit (Pettit G.R., Clewlow P.W., Dufresne C., et al. Isolation and structure of the cyclic peptide hymenistatin I . Can. J. Chem. 1990, 68: 708-711.). The sequence of the peptide chain is: cyclo(Pro-Pro-Tyr-Val-Pro-Leu-Ile-Ile). For the convenience and accuracy of discussion, the amino acid residues are numbered, that is, HS-1 is expressed as (Ile 1 -Ile 2 -Pro 3 -Pro 4 -Tyr 5 -Val 6 -Pro 7 -Leu 8 ). [0003] It has been reported that HS-1 has an inhibitory effect on cell growth in the study of P388 in mouse lymphoblastic non-leukemic leukemia, but the results have not been fully confirmed in subsequent studies. [0004] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/64C07K1/02C07K1/20A61P37/06
CPCY02P20/55
Inventor 李湘徐琪
Owner CHINESE PEPTIDE CO
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