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A kind of liquid phase synthesis method of acetyl tetrapeptide-2

A technology of acetyl tetrapeptide and liquid phase synthesis, which is applied to the preparation method of peptides, chemical instruments and methods, peptides, etc., can solve the problem of high synthesis cost, and achieve the effect of simple synthesis method, reduced production cost, and reduced synthesis cost

Active Publication Date: 2021-06-04
SHAANXI HUIKANG BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis cost of this method is high

Method used

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  • A kind of liquid phase synthesis method of acetyl tetrapeptide-2
  • A kind of liquid phase synthesis method of acetyl tetrapeptide-2

Examples

Experimental program
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Effect test

Embodiment 1

[0034] 1. Synthesis of Ac-D-Lys(Boc)-Asp(OtBu)-OH

[0035] (1) Synthesis of Ac-D-Lys(Boc)-OH

[0036] Mix and dissolve 24.6g (100mmol) H-D-Lys(Boc)-OH with 180mL dichloromethane and 8.7mL (50mmol) N,N'-diisopropylethylamine, then add 11.3mL (120mmol) acetic anhydride, room temperature React for 1 hour; concentrate the reaction liquid, add diethyl ether to make a slurry, filter, wash the filter cake, and dry under vacuum at room temperature to obtain 17.9 g of Ac-D-Lys(Boc)-OH.

[0037] (2) Synthesis of Ac-D-Lys(Boc)-COOSu

[0038] Mix 17.9g (95mmol) Ac-D-Lys(Boc)-OH, 200mL tetrahydrofuran and 12.0g (105mmol) N-hydroxysuccinimide until dissolved, then add 17.8g (114mmol) dicyclohexylcarbodiimide Amine was reacted at room temperature for 4 hours. After the reaction, solid-liquid separation was carried out to obtain a tetrahydrofuran solution of Ac-D-Lys(Boc)-COOSu.

[0039](3) Synthesis of Ac-D-Lys(Boc)-Asp(OtBu)-OH

[0040] Add 180mL of a mixed aqueous solution containing 1...

Embodiment 2

[0055] 1. Synthesis of Ac-D-Lys(Boc)-Asp(OtBu)-OH

[0056] (1) Synthesis of Ac-D-Lys(Boc)-OH

[0057] Mix and dissolve 24.6g (100mmol) H-D-Lys(Boc)-OH with 200mL dichloromethane and 12.1mL (70mmol) N,N'-diisopropylethylamine, then add 12.3mL (130mmol) acetic anhydride, room temperature The reaction was carried out for 2 hours; after the reaction solution was concentrated, diethyl ether was added to make a slurry, filtered, the filter cake was washed, and vacuum-dried at room temperature to obtain 17.5 g of Ac-D-Lys(Boc)-OH.

[0058] (2) Synthesis of Ac-D-Lys(Boc)-COOSu

[0059] Mix 17.5g (93mmol) Ac-D-Lys(Boc)-OH, 200mL tetrahydrofuran and 12.8g (112mmol) N-hydroxysuccinimide until dissolved, then add 18.8g (121mmol) dicyclohexylcarbodiimide Amine was reacted at room temperature for 4 hours. After the reaction, solid-liquid separation was performed to obtain a tetrahydrofuran solution of Ac-D-Lys(Boc)-COOSu.

[0060] (3) Synthesis of Ac-D-Lys(Boc)-Asp(OtBu)-OH

[0061] Add...

Embodiment 3

[0076] 1. Synthesis of Ac-D-Lys(Boc)-Asp(OtBu)-OH

[0077] (1) Synthesis of Ac-D-Lys(Boc)-OH

[0078] Mix and dissolve 24.6g (100mmol) H-D-Lys(Boc)-OH with 200mL dichloromethane and 13.8mL (80mmol) N,N'-diisopropylethylamine, then add 14.2mL (150mmol) acetic anhydride, room temperature The reaction was carried out for 1.5 hours; after the reaction solution was concentrated, diethyl ether was added to make a slurry, filtered, the filter cake was washed, and vacuum-dried at room temperature to obtain 17.3 g of Ac-D-Lys(Boc)-OH.

[0079] (2) Synthesis of Ac-D-Lys(Boc)-COOSu

[0080] Mix 17.3g (92mmol) Ac-D-Lys(Boc)-OH, 200mL tetrahydrofuran and 13.8g (120mmol) N-hydroxysuccinimide until dissolved, then add 20.1g (129mmol) dicyclohexylcarbodiimide Amine was reacted at room temperature for 6 hours. After the reaction, solid-liquid separation was carried out to obtain a tetrahydrofuran solution of Ac-D-Lys(Boc)-COOSu.

[0081] (3) Synthesis of Ac-D-Lys(Boc)-Asp(OtBu)-OH

[0082]...

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Abstract

The invention discloses a liquid-phase synthesis method of acetyl tetrapeptide-2, which synthesizes two N-terminal or side chain protected small fragment peptides: Ac-D-Lys(Boc)-Asp(OtBu )‑OH and H‑Val‑m‑Tyr‑OMe, and then condense the small fragment peptides, complete carbon-terminal amidation by transesterification to obtain the protected target product, and then deprotect to obtain the crude product of acetyl tetrapeptide‑2 , the crude product was purified to obtain the pure product of acetyl tetrapeptide-2. The synthesis method of the invention avoids the use of expensive resins in the solid-phase method, overcomes the disadvantages of using protected amino acids in each step of the solid-phase method, and consumes too much reagent, reduces the cost, and has the advantages of simple synthesis method, energy saving and environmental protection.

Description

technical field [0001] The invention belongs to the technical field of polypeptide synthesis, and in particular relates to a method for synthesizing acetyl tetrapeptide-2 through a liquid phase method. Background technique [0002] Acetyl tetrapeptide-2 is an active polypeptide containing 4 amino acids, the amino acid sequence is: Ac-D-Lys-Asp-Val-m-Tyr-NH 2 , is the modification of the 33-36 amino acid sequence of thymopoietin II, which has a certain role in regulating the immune function of the body and can enhance the immune defense of the skin; it can enhance the natural factors that maintain the collagen level and the correct assembly of elastic fibers, and promote The combination of cells and extracellular matrix counteracts adverse effects that lead to loss of skin firmness and adhesion, thereby improving skin condition; it is mainly manifested in the increase of epidermal thickness and the repair of epidermal skin texture. The main applications of acetyl tetrapeptid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/11C07K1/06C07K1/02
Inventor 王慧张忠旗高长波王斌张博韩广郭添赵金礼杨小琳
Owner SHAANXI HUIKANG BIO TECH CO LTD
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