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Process for solid-phase microwave synthesis of polypeptide

A solid-phase synthesis and microwave technology, applied in the fields of organic chemistry and medicinal chemistry, can solve the problems of long peptide preparation process time, high amino acid excess multiple, increase peptide synthesis cost, etc., to improve the purity and yield, and shorten the reaction. time, the effect of shortening the synthesis cycle

Inactive Publication Date: 2005-11-23
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the main problems in the solid-phase peptide synthesis are that the reaction speed is slow due to the mass transfer between solid and liquid, and the connection time of each amino acid is two hours or more, and the peptide preparation process takes a long time; Increased peptide synthesis cost due to high amino acid excess

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 The microwave method preparation of thymopentin

[0023] (1) Weigh 3 grams (2.79 mmol) of Wang resin (0.93 mmol / g), place it in a reactor, add 15 mL of dichloromethane to swell the resin for 120 minutes, and remove the dichloromethane solution. Weigh 19.53mmol Fmoc-Tyr(tBu)-OH (protected tyrosine), add 10mL tetrahydrofuran to dissolve, then add 19.53mmol diisopropylcarbodiimide and 19.53mmol 1-hydroxybenzotriazole, react 150min. After the reaction, the precipitate was filtered out, and the filtrate was added to the resin, and 1.395 mmol of dimethylaminopyridine was added at the same time, and the reaction was carried out for 20 hours. The ratio of the amount of each material substance in the reaction is Fmoc-Tyr (tBu)-OH: resin=7: 1; Fmoc-Tyr (tBu)-OH: condensation reagent=1: 1; Dimethylaminopyridine: resin=0.5: 1. After the reaction, the reaction solution was filtered off, and 15 mL of dichloromethane, methanol, and dimethylformamide were added to wash ...

Embodiment 2

[0033] Example 2 The microwave method synthesis of thymopentin under double excess of amino acid and condensation reagent

[0034] (1) Weigh 1 gram (0.93 mmol) of King Resin (0.93 mmol / g), place it in a reactor, add 10 mL of dichloromethane to swell the resin for 90 minutes, and remove the dichloromethane solution. Weigh 3.4875mmol Fmoc-Tyr(tBu)-OH, add 10mL dimethylformamide to dissolve, then add 4.185mmol diisopropylcarbodiimide and 4.185mmol 1-hydroxybenzotriazole, and react for 30min. After the reaction, the precipitate was removed by filtration, and the filtrate was added to the resin, and 0.465 mmol of dimethylaminopyridine was added at the same time, and the reaction was carried out for 4 hours. The ratio of the amount of each material in the reaction is amino acid: resin = 3: 1; Fmoc-Tyr (tBu) -OH: condensation reagent = 1: 1.2; dimethylaminopyridine: resin = 0.1: 1. After the reaction, the reaction solution was filtered off, and 10 mL of dichloromethane, methanol, an...

Embodiment 3

[0046] Example 3 Microwave-assisted solid-phase synthesis of octreotide

[0047] (1) Weigh 1 g (0.4 mmol) of Rink Amide resin (0.4 mmol / g), place it in a reactor, add 5 mL of dichloromethane to swell the resin for 30 minutes, and suck out the dichloromethane solution. Weigh 1.6mmol of the bisacetal formed by Fmoc-L-threoninol and p-carboxybenzaldehyde, add 8mL of N-methylpyrrolidone to dissolve, then add 1.76mmol of dicyclohexylcarbodiimide and 1.76mmol of 1-hydroxybenzene And triazole, reaction 30min. After the reaction, the precipitate was removed by filtration, and the filtrate was added to the resin, and 0.08 mmol of dimethylaminopyridine was added at the same time, and the reaction was carried out for 4 hours. The ratio of the amount of each material in the reaction is amino acid: resin = 4: 1; threonine acetal: condensation reagent = 1: 1.1; dimethylaminopyridine: resin = 0.2: 1. After the reaction, the reaction solution was filtered off, and 10 mL of dichloromethane, ...

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Abstract

Disclosed is a process for solid-phase microwave synthesis of polypeptide comprising, (1) preparing amino acid and resin compound, (2) removing amino protecting group through microwave radiation, (3) condensating amino acid through microwave radiation, (4) replacing amino acids, repeating step (2) and (3) to synthesize the needed polypeptides, (5) preparing the polypeptides crude product.

Description

technical field [0001] The polypeptide microwave solid-phase synthesis method relates to a microwave-assisted solid-phase synthesis method for polypeptides, and the invention belongs to the fields of organic chemistry and pharmaceutical chemistry. Background technique [0002] Generally speaking, a polypeptide refers to a compound composed of less than fifty amino acids, which has a variety of biological activities. It has been found that there are tens of thousands of polypeptides in living organisms, and it is found that all cells can synthesize polypeptides. At the same time, almost all cells are also regulated by polypeptides, which involve various fields such as hormones, nerves, cell growth and reproduction. They are important chemical messengers that communicate information between cells and organs. They perform their subtle information transmission functions through endocrine, neuroendocrine and even neurosecretion, so that organisms can be combined into a series of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K1/04
CPCY02P20/55
Inventor 沈树宝王卫国李佩华应汉杰欧阳平凯
Owner NANJING UNIV OF TECH
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