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Synthesis method of snake venom-like tripeptide

A synthetic method, snake venom technology, applied in the field of polypeptide liquid phase synthesis, can solve the problems of high price of Pd/C, potential safety hazards of cosmetics, high synthesis cost, etc., and achieve the effect of market competitiveness, easy scale-up synthesis, and controllable process

Pending Publication Date: 2022-03-22
上海予利生物科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Boc protection method contains an unnatural amino acid Dab in the sequence, which is an amino acid containing two amino groups. It involves the selective protection of one of the amino groups by Boc, which makes the synthesis cost of preparing suitable side chain protection Dab high, and also restricts the snake venom tripeptide. Synthesis cost Main raw materials, such as Dab(Boc)-OMe synthesis is difficult and expensive
However, the final removal of Cbz using the Cbz protection method requires the use of Pd / C and heavy metals, which have certain safety hazards for cosmetics, and the price of Pd / C is also very expensive.

Method used

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  • Synthesis method of snake venom-like tripeptide
  • Synthesis method of snake venom-like tripeptide
  • Synthesis method of snake venom-like tripeptide

Examples

Experimental program
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Effect test

Embodiment 1

[0045] A synthetic method of snake venom tripeptide, comprising the following steps:

[0046] (1) Synthesis of 3-phthalimide propionyl chloride:

[0047] Put 20 grams of 3-phthalimidopropionic acid into a 500 ml reaction bottle, add 100 ml of toluene, seal it, add 40 ml of thionyl chloride, stir, stir at room temperature for 1 hour, and then heat to 60°C React for 2-3 hours, then reflux for 6-8 hours. After the reaction is finished, thionyl chloride and toluene are recovered under reduced pressure and recovered to dryness as much as possible. Inhale 100 ml of dichloromethane, stir to dissolve.

[0048] (2) Synthesis of 3-phthalimidopropionylproline:

[0049]Add 23 grams of sodium carbonate to 100 milliliters of water, stir until completely dissolved, add 15 grams of L-proline and stir, cool to below 20°C, add dropwise 3-phthalimidopropionyl chloride obtained in step (1) dichloromethane solution, reacted at room temperature, maintained the pH value at 9-10, added dropwise, ...

Embodiment 2

[0063] Condensation reaction:

[0064] Combine 6 grams of 3-phthalimidopropionylproline obtained in step (2) of Example 1 with the side chain phthaloyl-protected L-2,4 obtained in step (5) of Example 1 - Add 5 grams of diaminobutyrylbenzylamine hydrochloride into a 250 ml three-necked reaction flask, add 80 ml of DMF, then add 10 grams of condensing agent HBTU, and 2 ml of triethylamine for condensation reaction at room temperature, react for 4-8 hours, then add 100 milliliters of water, add 100 milliliters of ethyl acetate to extract 3 times, the ethyl acetate layer is washed with water 3 times, 0.5N hydrochloric acid 3 times, 5% sodium carbonate aqueous solution 3 times, saturated saline 3 times, then add anhydrous sodium sulfate It was dried, filtered, and concentrated to obtain 9.5 g of an oily product with a purity of 97.2% by HPLC.

[0065] Synthesis of snake venom-like tripeptide hydrochloride:

[0066] With gained free snake venom tripeptide 5 grams. Add 5 ml of hyd...

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Abstract

The invention relates to a synthetic method of snake venom-like tripeptide, which comprises the following steps: by taking 3-phthalimidopropionic acid as an initial raw material, performing acylating chlorination, condensing with proline, and condensing an obtained fragment with L-2, 4-diaminobutyryl benzylamine hydrochloride with a side chain protected by phthaloyl, thereby obtaining the phthaloyl-protected snake venom-like tripeptide. Finally, a phthaloyl protecting group is removed through hydrazine, and then the free snake venom-like tripeptide is obtained. The free snake venom-like tripeptide is obtained after a phthaloyl protecting group is removed by hydrazine, and can be conveniently prepared into acetate and hydrochloride products. Compared with the prior art, the method has the advantages of easily available raw materials, high product purity, simplicity and convenience in operation and suitability for industrial production.

Description

technical field [0001] The invention belongs to the field of polypeptide liquid-phase synthesis, and relates to a synthesis method of a snake venom-like tripeptide, in particular to a synthesis method of a free snake venom-like tripeptide. Background technique [0002] Like snake venom tripeptide, its free chemical structural formula is as follows: [0003] [0004] Sequence expression: Beta-Ala-Pro-Dab-NHBzl, is a small peptide that mimics the activity of snake venom Waglerin I. Clinical trials have shown that snake venom tripeptide can reduce the generation of wrinkles by inhibiting muscle contraction, and has excellent smoothness and rapidity. Anti-wrinkle effect. A group of substances that cause skin tightening, making loose skin firmer and more elastic, and a cosmetic method that can increase the collagen content of the skin, are now popular in luxury skin care products of international brands. The traditional synthesis method is through solid-phase synthesis. Due ...

Claims

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Application Information

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IPC IPC(8): C07K5/023C07K1/30C07K1/06C07K1/02
CPCC07K5/0202Y02P20/55
Inventor 金健林严承飞金萍
Owner 上海予利生物科技股份有限公司
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