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A kind of preparation method of acetyl tetrapeptide-2

A technology of acetyl tetrapeptide and acetonitrile, applied in the field of preparation of acetyl tetrapeptide-2, can solve the problems of high synthesis cost and high price, and achieve the effects of simple operation, easy operation and cost reduction

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

[0003] At present, the preparation of acetyl tetrapeptide-2 uses a classic solid-phase synthesis method. Because the protected amino acid product Fmoc-L-m-Tyr(tBu)-OH is expensive, the synthesis cost is very high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1. Synthesis of Fmoc-L-m-Tyr(TBDMS)-OH by liquid phase method

[0033] (1) Synthesis of Fmoc-L-m-Tyr-OH

[0034] Weigh 10.9g (60mmol) of L-m-Tyr-OH into a 1L eggplant-shaped bottle, add 100mL of water and 18mL of triethylamine to make the pH between 8 and 9, dissolve until clear; weigh 21.9g (65mmol) of fluorenylmethoxycarbonyl Add 250mL of acetonitrile to a 500mL Erlenmeyer flask, dissolve and clarify it, then immediately add it into an eggplant-shaped flask, stir for 0.5 hours, measure the pH value, adjust it with triethylamine, and keep it at 8-9. Continue to stir the reaction for 3 hours, TLC (developing agent is: petroleum ether: ethyl acetate: formic acid volume ratio = 10:30:1) shows that the reaction is complete, adjust the pH<5 with 1mol / L hydrochloric acid, stir for 15 minutes, at 40 ° C Rotary evaporate at low temperature until no distillate is produced, add 300mL 1mol / L potassium bisulfate aqueous solution and 600mL ethyl acetate for extraction, collect the...

Embodiment 2

[0048] 1. Synthesis of Fmoc-L-m-Tyr(TBDMS)-OH by liquid phase method

[0049] (1) Synthesis of Fmoc-L-m-Tyr-OH

[0050] Weigh 7.3g (40mmol) of L-m-Tyr-OH into a 1L eggplant-shaped bottle, add 70mL of water and 10mL of triethylamine to make the pH between 8 and 9, and dissolve until clear; weigh 17.5g (52mmol) of fluorenmetoxycarbon Add 70mL of acetonitrile to a 500mL Erlenmeyer flask, dissolve and clarify it, then immediately add it to an eggplant-shaped flask, stir for 0.5 hours, measure the pH value, adjust it with triethylamine, and keep it at 8-9. Continue to stir the reaction for 3 hours, TLC (developing agent is: petroleum ether: ethyl acetate: formic acid volume ratio = 10:30:1) shows that the reaction is complete, adjust the pH<5 with 1mol / L hydrochloric acid, stir for 15 minutes, at 40 ° C Rotary evaporate at low temperature until no distillate is produced, add 300mL 1mol / L potassium bisulfate aqueous solution and 500mL ethyl acetate for extraction, collect the ethyl...

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Abstract

The invention discloses a preparation method of acetyl tetrapeptide-2. In the method, Fmoc-L-m-Tyr-OH, tert-butyldimethylchlorosilane and N,N diisopropylethylamine are reacted to synthesize Fmoc‑L‑m‑Tyr(TBDMS)‑OH, then connect Fmoc‑L‑m‑Tyr(TBDMS)‑OH, Fmoc‑Val‑OH, Fmoc‑Asp(OtBu)‑on Rink‑Amid‑AM Resin in sequence OH, Fmoc‑D‑Lys(Boc)‑OH, deprotected and cleaved to obtain the acetyl tetrapeptide‑2 product. The present invention combines solid-phase synthesis with liquid-phase synthesis, and first synthesizes Fmoc-L-m-Tyr(TBDMS)-OH through a liquid-phase synthesis method, and then synthesizes acetyl tetrapeptide-2 through a classic solid-phase synthesis method. The advantages of cost reduction and easy operation, as well as the characteristics of high synthesis efficiency and simple operation of the classic solid-phase method, are a relatively ideal method for the synthesis of acetyl tetrapeptide-2.

Description

technical field [0001] The invention belongs to the technical field of cosmetics, and in particular relates to a preparation method of acetyl tetrapeptide-2. Background technique [0002] Acetyl tetrapeptide-2 is an active polypeptide composed of four amino acids, its sequence is Ac-D-Lys-Asp-Val-L-m-Tyr-NH 2 , is a four-amino acid peptide chain derived from the nitrogen terminal of thymopoietin II (AA33~36), which can stimulate the growth and differentiation of keratinocytes, effectively strengthen skin immune defense and promote epidermal regeneration, and enhance skin system immunity force. Therefore, it is mostly used in cosmetics to develop anti-aging beauty products. [0003] At present, the classic solid-phase synthesis method is used for the preparation of acetyl tetrapeptide-2. Because the protected amino acid product Fmoc-L-m-Tyr(tBu)-OH is expensive, the synthesis cost is very high. Contents of the invention [0004] The technical problem to be solved by the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/11C07K1/16C07K1/06C07K1/04C07K1/02
CPCC07K5/1019Y02P20/55
Inventor 王万科张忠旗郭添王昕常刚高长波王斌杨小琳赵金礼
Owner SHAANXI HUIKANG BIO TECH CO LTD
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