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Method for preparing immune seven peptides

A technology of heptapeptide and resin, which is applied in the field of preparation of immune heptapeptide, can solve the problems of unnecessary optimization, small output, and limited optimization process, etc.

Inactive Publication Date: 2011-11-02
程云 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] This process usually does not have to be optimized for small-scale production in the laboratory, although the unit cost is high, the overall cost is not high because the required output is small
Therefore, there are few instructions for optimizing solid-phase synthesis of polypeptides in the prior art, and a large number of condition selections also limit the optimization process, especially most of the optimizations are only laboratory optimizations. Once scaled up, the yield will drop sharply

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1 Synthesis process of immune heptapeptide of 1 gram grade dichloro resin

[0105] (1) Preparation of Fmoc-Gly-resin

[0106] Weigh 1 g of 2-chloro-trityl chloromethyl resin (loading capacity: 1.0 mmol / g) and inject it into the reaction column, add 10 ml of DCM, soak at room temperature for 30 minutes and then dry it with a vacuum pump, add Fmoc-Gly-OH 0.3 g, DIEA 0.8ml, and DCM 10ml, react at room temperature for 1.5 hours, then add blocking reagent methanol 3ml and react at room temperature for 0.5 hours, the resin is washed with 10ml DMF for 3 times, 10ml isopropanol for 3 times, redistilled 5ml DMF for 2 times times, drained to obtain Fmoc-Gly-resin;

[0107] (2) Preparation of Fmoc-Ser(tBu)-Gly-resin

[0108] Add 7.5ml of decapping reagent (20% piperidine in DMF solution (v / v)) to the Fmoc-Gly-resin in step (1), react at room temperature for 5 minutes, drain, and add 7.5ml of the decapping reagent to react at room temperature For 20 minutes, wash wit...

Embodiment 2

[0129] Example 2 Microwave solid-phase synthesis of immune heptapeptide

[0130] Described method is substantially identical with embodiment 1, and difference is:

[0131] (1) In each step (2)-(8) of Example 1, the process of "adding 7.5ml decapping reagent (20% piperidine in DMF (v / v))" until the end of this step is replaced by:

[0132] Add 7.5ml decapping reagent (20% piperidine in DMF solution (v / v)), and then place it in a microwave reactor (VOYAGER product Explorer 12) for reaction. The microwave conditions are: temperature is 55°C, reaction time is 5min, and the After completion, filter and extract the solution, wash the resin once with 3ml dimethylformamide, 3ml methanol, and 3ml methylene chloride successively, add the same amount of Fmoc-protected amino acids as in Example 1 (as in Example 1 step ( 2) Fmoc-Ser(tBu)-OH in , and so on for other steps) and DIEA were placed in the above-mentioned microwave reactor for reaction. The microwave conditions were: the tempera...

Embodiment 3

[0136] Example 3 Industrial-scale synthetic process of immune heptapeptide

[0137] The laboratory-level preparation in Example 1 is directly expanded by 20 times for large-scale production, that is, 20 grams of 2-chloro-triphenylchloromethyl resin (loading capacity: 1.0 mmol / g) is weighed and injected into the corresponding industrial reaction column , unless otherwise specified, the required reagents are 20 times that of Example 1, the conditions are the same as in Example 1, and the corresponding steps (1)-(9) are carried out to obtain 13g of crude immune heptapeptide with a purity of 80.5%. It can be seen that, according to the optimized conditions of the present invention, the scale-up production can be directly carried out, and its yield and purity will not cause loss during the scale-up.

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PUM

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Abstract

The invention belongs to the field of preparation of polypeptide, and in particular relates to a method for preparing immune seven peptides GQTYTSG.

Description

technical field [0001] The invention belongs to the field of polypeptide preparation, in particular, the invention relates to a preparation method of immune heptapeptide. Background technique [0002] The peptide whose sequence is GQTYTSG (abbreviated as "immune heptapeptide" or 7P herein) is an immunogenic peptide originally designed according to hepatitis C virus. 7P and its derivatives of immunogenic peptides of hepatitis virus. In addition, in PCT application WO / 2007 / 137456, the inventors also found that 7P and its derivatives can also be used for the prevention and treatment of liver damage, especially for the prevention or treatment of immune liver damage and hepatotoxic chemical substances. of liver damage. In addition, in recent years, it has also been found that it can treat nephritis and pneumonia. [0003] The solid-phase synthesis of polypeptides is a long-established technology, usually based on trityl chloromethyl resin, 4-methyl-trityl chloromethyl resin, 4...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/16C07K1/06C07K1/04
Inventor 王增禄程云张英起杨塞赵宁
Owner 程云
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