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A kind of large-scale synthetic method of ajirelin

A synthetic method, the technology of dimethylformamide, applied in the field of peptide synthesis, can solve the problems of long synthesis period, high carrier cost, and low loading capacity, and achieve the effects of increased yield, reduced difficulty, and increased total yield

Active Publication Date: 2021-03-26
SHAANXI HUIKANG BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to overcome the disadvantages of high carrier cost and low loading capacity of the traditional classic solid-phase synthesis method in the prior art, and the disadvantages of long synthesis cycle and low efficiency of the liquid-phase synthesis method, and provide a simple process method , low production cost, easy to purify, and high-efficiency synthetic method of ajirelin, the present invention reduces production cost, improves production efficiency, and has great significance for the establishment of large-scale synthesis process research and application

Method used

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  • A kind of large-scale synthetic method of ajirelin
  • A kind of large-scale synthetic method of ajirelin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: a kind of large-scale synthesis method of ajirelin

[0049] The large-scale synthetic method of ajirelin is as follows:

[0050] (1) Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-2-Chlorotrityl Chloride Resin;

[0051] (2) Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-OH;

[0052] (3) Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-NH 2 ;

[0053] (4) Synthesis of Ac-Glu-Glu-Met-Gln-Arg-Arg-NH 2 .

Embodiment 2

[0054] Embodiment 2: Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-2-Chlorotrityl Chloride Resin

[0055] On the basis of the technical solution provided in Example 1, this example further revolves around Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-2-Chlorotrityl Chloride Resin The synthesis of the specific synthesis steps are as follows:

[0056] (1) Synthesis of Fmoc-Arg(Pbf)-2-Chlorotrityl Chloride Resin

[0057] Add 100.0g 2-Chlorotrityl Chloride Resin to the synthesizer, add 1000mL dichloromethane to soak and swell for 15 minutes, then filter with suction, add 1000mL dichloromethane, 114.2g (0.176mol) Fmoc-Arg(Pbf) to the synthesizer -OH, 105ml (0.64mol) N,N´-diisopropylethylamine, under the protection of nitrogen, stirred at room temperature for 2 hours, blocked with anhydrous methanol for 0.5 hours, filtered with suction, and washed twice with isopropanol ( Wash twice with 800ml each time) and N,N-dimethylformamide (800ml each time) to o...

Embodiment 3

[0064] Example 3: Synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-OH

[0065] On the basis of the technical solution provided in Example 1, this example further revolves around the synthesis of Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-OH, specifically The synthesis steps are as follows:

[0066] Add the dried Ac-Glu(OtBu)-Glu(OtBu)-Met-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-2-Chlorotrityl Chloride Resin into a 2L beaker, add 200ml of trifluoroethanol, Acetic acid 75ml, dichloromethane 725ml cutting solution, cracking resin, stirring reaction for 2 hours, filtering, filter cake washed three times with dichloromethane, each 100ml, combined filtrate, filtrate was washed twice with saturated sodium bicarbonate solution, each 700ml Use saturated sodium bicarbonate solution to pH = 6, adjust pH = 7 with 800ml of saturated saline, combine the water phase and filtrate into an eggplant-shaped bottle, add 500ml of saturated saline, remove the organic solvent under r...

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Abstract

The invention discloses a large-scale synthesis method of argireline. The preparation method comprises the following steps: by taking 2 Chlorotrityl Chloride Resin as a carrier, carrying out solid-phase synthesis to obtain fully-protected fragment peptidic acid, carrying out a liquid-phase amidation reaction on a carboxyl terminal by taking the fully-protected peptidic acid fragment as a raw material to obtain fully-protected amide, and carrying out deprotection to obtain the target peptide. Compared with amino resin commonly used in an existing synthesis method, the selected resin carrier islow in price, and the uploading amount is increased by nearly one time; a selected ammonia reagent for the an amidation reaction is cheap, easy to obtain and short in amidation reaction time, and hydrolysis of ester is inhibited.In the cutting post-treatment process, anhydrous ether is abandoned, so that the safety is high, and the method is environment-friendly. The method overcomes the problemsof high cost and low loading capacity of the existing classic solid-phase synthetic resin, also overcomes the defects of complex liquid-phase synthesis process, long synthesis period and low efficiency, has the advantages of low synthesis cost, high synthesis efficiency and simple synthesis method, and can be used for large-scale synthesis of the argireline.

Description

technical field [0001] The invention belongs to the technical field of polypeptide synthesis, and in particular relates to a solid-liquid combination aquirelin synthesis method. Background technique [0002] Argireline—Argireline, is an active polypeptide with anti-wrinkle function, the sequence is Ac-Glu-Glu-Met-Gln-Arg-Arg-NH 2 , is a safe substitute for botulinum toxins. Because it can block the information transmission between neuromuscular and avoid excessive muscle contraction, the newly synthesized collagen under the skin can be rearranged, and wrinkles can be relieved or even eliminated. Therefore, it is mostly used in cosmetics as an anti-wrinkle ingredient. [0003] At present, the synthesis methods of ajirelin mainly include solid-phase synthesis and liquid-phase synthesis. There are different defects in the synthetic methods of several ajirelin disclosed at present. For example, the publication number is the preparation method described in the patent document ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/36C07K1/30C07K1/20C07K1/16C07K1/06C07K1/04C07K1/02
CPCC07K7/06Y02P20/55
Inventor 李晨梁强王昕张忠旗陈科杨小琳赵金礼
Owner SHAANXI HUIKANG BIO TECH CO LTD
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