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Method for efficiently preparing palmitoyl tripeptide-5 based on activated ester

A technology of palmitoyl tripeptide and activated ester is applied in the preparation methods of peptides, chemical instruments and methods, peptides, etc., to achieve the effects of high yield, high product purity and simple operation.

Active Publication Date: 2019-11-08
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, there are very few literature reports about the preparation of palmitoyl tripeptide-5 in the prior art. It is mentioned in US2007099842A1 that the preparation of palmitoyl tripeptide-5 by solid-phase synthesis method needs a variety of protecting groups and removal methods. protected reagents, and the final yield was only 19%
In addition to this method, there is no other report on the preparation of palmitoyl tripeptide-5

Method used

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  • Method for efficiently preparing palmitoyl tripeptide-5 based on activated ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] (1), the preparation of palmitoyl chloride (Pal-Cl)

[0063] In a 250mL single-necked round-bottom flask, add 20.52g of palmitic acid, add 60mL of thionyl chloride to dissolve, reflux at 80°C for 5 hours, cool to room temperature, spin dry the solvent, and obtain the target product palmitoyl chloride (21.6g, 98%) in white oil . 1 H NMR (CDCl 3 ,300MHz)δ0.86-0.90(t,3H),1.26-1.34(m,24H),1.66-1.75(m,2H),2.86-2.90(t,2H).

[0064] (2), preparation of Pal-Lys(Cbz)-OH

[0065] 500mL single-necked round bottom flask, weigh 21g Na 2 CO 3 Dissolve in 120mL water, add 60mL tetrahydrofuran, then add 11g N ε -Cbz-L-lysine was dissolved, and at room temperature, 60 mL of tetrahydrofuran solution containing 11.2 g of palmitoyl chloride was added dropwise. After the dropwise addition was completed, the reaction was stirred for 16 h. After the reaction, use 1M HCl to adjust the pH of the system to 3~4, extract with dichloromethane, dry over anhydrous sodium sulfate, filter and spi...

Embodiment 2

[0077] (1), the preparation of palmitoyl chloride (Pal-Cl)

[0078] Add 20.52g of palmitic acid and 160mL of dichloromethane into a 250mL single-necked round-bottom flask, add 14mL of oxalyl chloride and 2 drops of N,N-dimethylformamide dropwise under ice-bath conditions, and gradually return to room temperature after the addition and stir for reaction 18 hours, after the reaction was completed, the solvent was spin-dried to obtain the target product palmitoyl chloride (19.8 g, 90%) in the form of white oil. 1 H NMR (CDCl 3 ,300MHz)δ0.86-0.90(t,3H),1.26-1.34(m,24H),1.66-1.75(m,2H),2.86-2.90(t,2H).

[0079] (2), preparation of Pal-Lys(Cbz)-OH

[0080] Weigh 29g NaOH in a 500mL single-necked round bottom flask, add 100mL water, then add 21g N ε -Cbz-L-lysine was dissolved, and at room temperature, 100 mL of tetrahydrofuran solution containing 19.8 g of palmitoyl chloride was added dropwise, and after the dropwise addition was completed, the reaction was stirred for 18 h. Aft...

Embodiment 3

[0092] (1), the preparation of palmitoyl chloride (Pal-Cl)

[0093] Weigh 25.6g of palmitic acid in a 500mL single-necked round-bottom flask, add 200mL of chloroform to dissolve, and add 100mL of chloroform solution containing 25g of phosphorus pentachloride dropwise to the reaction system under ice bath conditions. After reaching room temperature, the reaction was stirred for 12 hours, and the solvent was spin-dried to obtain the target product palmitoyl chloride (25 g, 90%) in the form of white oil. 1 H NMR (CDCl 3 ,300MHz)δ0.86-0.90(t,3H),1.26-1.34(m,24H),1.66-1.75(m,2H),2.86-2.90(t,2H).

[0094] (2), preparation of Pal-Lys(Cbz)-OH

[0095] Weigh 30g K 2 CO 3 and 20g N ε -Cbz-L-Lysine was dissolved in a 500mL single-necked round-bottom flask by adding 120mL of water and 60mL of tetrahydrofuran. Under the condition of ice-water bath, slowly add 60mL of tetrahydrofuran solution containing 20g of palmitoyl chloride dropwise. After the dropwise addition, gradually return t...

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Abstract

The invention relates to a method for efficiently preparing palmitoyl tripeptide-5 based on an activated ester, and belongs to the technical field of polypeptide preparation. The method for efficiently preparing the palmitoyl tripeptide-5 based on the activated ester comprises the steps: palmitic acid and an amino acid are taken as raw materials, a palmitoyl tripeptide fragment is prepared throughcombination of acyl chloride and the activated ester, then protecting groups are removed through a hydrogenation reaction, and a final product, namely the palmitoyl tripeptide-5 is obtained. According to the method, repeated operation of protection and de-protection in other methods is avoided, thus the cost is saved, and the efficiency is improved; and the method has the advantages of easy operation, high product purity, high yield, relatively low cost and the like, large-scale production can be achieved, and the palmitoyl tripeptide-5 can be industrially prepared.

Description

technical field [0001] The invention belongs to the technical field of polypeptide preparation, and in particular relates to a method for efficiently preparing palmitoyl tripeptide-5 based on activated esters. Background technique [0002] Palmitoyl tripeptide-5 (Palmitoyl-Lysyl-Valyl-Lysine, Pal-Lys-Val-Lys-OH) is also known as "tripeptide" or "collagen peptide COLL-O2" is the earliest and most widely used cosmetic peptide. Palmitoyl tripeptide-5 belongs to the signaling peptide, which can promote the synthesis of collagen (type Ⅰ, Ⅱ and Ⅳ) by increasing the activity of stromal cells and the production of extracellular matrix protein, making the skin look younger and more elastic. Adding it to cosmetics can help the skin replenish collagen, improve facial elasticity, and significantly reduce facial wrinkles. At the same time, it also has the ability to enhance cell activity , enhance skin moisture content, enhance skin luster, and improve skin tone. [0003] In the prior...

Claims

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Application Information

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IPC IPC(8): C07K5/09C07K1/08
CPCC07K5/0815Y02P20/55
Inventor 陶友华陈金龙王献红
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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