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RGD cyclic peptide synthesis method

A synthesis method and cyclic peptide technology, applied in the field of RGD cyclic peptide synthesis, can solve the problems of high cost and low product yield, and achieve the effects of low racemization rate, reduction of by-products and impurities, and high product yield

Active Publication Date: 2019-09-20
湖北强耀生物科技有限公司
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  • Application Information

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Problems solved by technology

In the traditional liquid-phase cyclization synthesis method, a condensation reagent needs to be added during the synthesis process, and the condensation reagent will bring by-products and impurities, resulting in low product yield and high cost

Method used

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Embodiment

[0043] The invention discloses a synthesis method of RGD cyclic peptide, comprising the following steps:

[0044] S1, Obtaining fully protected linear peptide

[0045] 1) Using Mtt-Lys(Boc)-OH as a starting material, an activating reagent is used to form an activated ester at the C-terminal of Mtt-Lys(Boc)-OH to obtain Mtt-Lys(Boc)-NHS;

[0046] 2) In an alkaline environment, add an amino acid to Mtt-Lys(Boc)-NHS, make the activated ester of Mtt-Lys(Boc)-NHS react with the amino group at the N-terminal of the amino acid, and form a connection;

[0047] 3) activating the carboxyl group of the amino acid to form an activated ester under the conditions of step S1, and connecting the N-terminal of the next amino acid to the C-terminal of the previous amino acid under the conditions of step S2;

[0048] 4) Using H-D-Phe-OMe as the terminal raw material, according to step 3), connect its N-terminal to the C-terminal of the previous amino acid to obtain a fully protected linear pept...

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Abstract

The invention discloses an RGD cyclic peptide synthesis method. The RGD cyclic peptide synthesis method comprises the following steps: S1, acquiring a fully protected linear peptide 1) to obtain Mtt-Lys (Boc)-NHS; 2) adding amino acid into Mtt-Lys (Boc)-NHS to achieve connection; 3) connecting the N end of a next amino acid to the C end of a previous amino acid; 4) taking H-D-Phe-OMe as a terminal raw material, and obtaining a fully protected linear peptide according to the step 3); S2, acquiring a fully protected cyclic peptide, and dissolving with DCM added with TFA to form an amide ring; S3, cutting and purifying; 5) placing the fully protected cyclic peptide therein for cutting for 2 hours; and 6) separating out by using ice ethyl ether, centrifuging to obtain polypeptide crude peptide, then washing by using ice ethyl ether for three times, removing part of impurities, drying under reduced pressure, and finally purifying by using HPLC to obtain a pure product. The method is simple to operate, pure in product, high in yield and low in racemization rate.

Description

technical field [0001] The invention relates to a method for synthesizing cyclic peptides, in particular to a method for synthesizing RGD cyclic peptides. Background technique [0002] The RGD sequence is a universal recognition site for extracellular matrix and integrins, which can increase the biological stability of peptides. RGD sequence peptide has a wide range of biological activities and can be used for the treatment of diseases such as cardiovascular disease, osteoporosis and inflammation, and can also prevent and treat tumors caused by abnormal cell adhesion, especially the metastasis of developing tumors; another On the one hand, RGD sequence peptides can be used as stimulants to promote the regeneration of damaged organs and tissues, wound healing, etc. RGD is a receptor for some integrins, and its selectivity depends partly on the conformation of RGD and the amino acids around RGD Residues. In the traditional liquid-phase cyclization synthesis method, a condens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/52C07K1/16C07K1/06C07K1/02
CPCC07K7/52Y02P20/55
Inventor 王钒钒卢然张中玉李广欢
Owner 湖北强耀生物科技有限公司