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Application of 1-Hydroxy-1,2,3-Benzotriazin-4(3h)-one in Polypeptide Synthesis

A technology for the synthesis of benzotriazine and peptides, which is applied in the field of amino acid peptides, can solve problems such as difficult to remove, low solubility, etc., and achieve the effect of low cost, simple process, and easy realization

Active Publication Date: 2016-01-13
合肥国肽生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the N,N'-dicyclohexylurea (DCU) produced by the reaction has very little solubility in most organic solvents, and sometimes it will be mixed in the product and it is difficult to remove

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1: Z-Phe-Leu-OMe

[0014] h 2 Preparation of N-Leu-OMe HCl: Under ice-water bath conditions, slowly drop 10.4ml (120mmol) thionyl chloride into a 250ml round-bottomed flask equipped with 100ml methanol and 13.2g (100mmol) leucine, drop After the addition, stir at room temperature for 4-5 hours, concentrate under reduced pressure to remove excess methanol, then repeatedly dissolve with methanol several times and concentrate under reduced pressure to remove excess hydrogen chloride, dissolve the product with a small amount of methanol, add ether dropwise to precipitate white crystals 17.2 g, yield 95%.

[0015] Preparation of Cbz-Phe-OH: Dissolve 19.8g (120mmol) of phenylalanine in 180ml of 2mol / L NaOH solution, cool in an ice-water bath to 0°C; then slowly add 10.2g (60mmol) of benzyloxycarbonyl chloride dropwise, Continue to stir for 0.5h after the dropwise addition; then slowly rise to room temperature, continue to stir for 2h; after the reaction, wash the re...

Embodiment 2

[0020] Example 2: Z-Val-Val-OMe

[0021] h 2 Preparation of N-Val-OMe HCl: Under ice-water bath conditions, slowly drop 5.2ml (60mmol) thionyl chloride into a 100ml round-bottomed flask equipped with 50ml methanol and 5.9g (50mmol) valine, drop After the addition, stir at room temperature for 4-5 hours, concentrate under reduced pressure to remove excess methanol, then repeatedly dissolve with methanol several times and concentrate under reduced pressure to remove excess hydrogen chloride, dissolve the product with a small amount of methanol, add ether dropwise to precipitate white crystals 7.9 g, yield 94%.

[0022] Preparation of Cbz-Val-OH: Dissolve 7.0g (60mmol) valine in 90ml 2mol / L NaOH solution, cool to 0°C in an ice-water bath; then slowly add 5.1g (30mmol) benzyloxycarbonyl chloride dropwise, drop Continue to stir for 0.5h after the addition; then slowly rise to room temperature, continue to stir for 2h; after the reaction, wash the reaction solution twice with 10ml...

Embodiment 3

[0027] Example 3: Z-Ala-Ala-OMe

[0028] h 2 Preparation of N-Ala-OMe HCI: under ice-water bath conditions, slowly drop 6.2ml (72mmol) thionyl chloride into a 120ml round bottom flask equipped with 60ml methanol and 5.4g (60mmol) alanine, drop After the addition, stir at room temperature for 4-5 hours, concentrate under reduced pressure to remove excess methanol, then repeatedly dissolve with methanol several times and concentrate under reduced pressure to remove excess hydrogen chloride, dissolve the product with a small amount of methanol, add ether dropwise to precipitate white crystals 7.5 g, yield 90%.

[0029] Preparation of Cbz-Ala-OH: Dissolve 6.4g (72mmol) of alanine in 108ml of 2mol / L NaOH solution, cool to 0°C in an ice-water bath; then slowly add 6.1g (36mmol) of benzyloxycarbonyl chloride dropwise, Continue to stir for 0.5h after the addition; then slowly rise to room temperature, continue to stir for 2h; after the reaction, wash the reaction solution twice with...

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PUM

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Abstract

The invention discloses application of 1-hydroxy-1,2,3-phentriazine-4(3H)-one in polypeptide synthesis. The application of 1-hydroxy-1,2,3-phentriazine-4(3H)-one in the polypeptide synthesis is characterized in that the application is mainly implemented by the following step of performing catalytic condensation on amino acid methyl ester hydrochloride and carbobenzoxy-protected amino acid through 1-hydroxy-1,2,3-phentriazine-4(3H)-one serving as a polypeptide condensating agent and 1-ethyl-(3-dimethyl amino propyl) carbonyl imine hydrochloride serving as a catalyst under conditions of an organic solvent and trifluoroacetic acid which is an organic acid to obtain polypeptides. The process for synthesizing the polypeptides by taking 1-hydroxy-1,2,3-phentriazine-4(3H)-one serving as the polypeptide condensating agent is simple, easy to implement and low in cost, and the yield of the polypeptides is high.

Description

technical field [0001] The invention relates to the technical field of amino acid polypeptides, in particular to the application of 1-hydroxyl-1,2,3-benzotriazin-4(3H)-one in polypeptide synthesis. Background technique [0002] Protein is one of the most basic substances that constitute a living body, and it plays a very important role in the processes of cell development, growth, and metabolism. Compared with proteins, the role of smaller polypeptides in organisms cannot be ignored. Peptides affect many important physiological and biochemical functions in organisms. They act as neurotransmitters, neuromodulators and hormones, and participate in receptor-mediated signal transduction. More than 100 active peptides are known to act in the central and peripheral nervous system, cardiovascular system, immune system and gut. In addition, peptides and peptide-based drugs have always been a research hotspot for pharmacologists. A small peptide consisting of 2-14 amino acids or w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K1/06C07K1/02C07K5/065C07K5/062
Inventor 张玮玮姜玉钦过治军王栋胡志国
Owner 合肥国肽生物科技有限公司