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A microwave-assisted method for preparing polypeptides

A microwave-assisted, polypeptide technology, which is applied in the field of microwave-assisted polypeptide preparation, can solve the problems of long polymerization reaction time, complicated and cumbersome operation, and low conversion rate of monomers, and achieve high industrial application value, simple experimental conditions, The effect of speeding up the reaction rate

Active Publication Date: 2022-01-14
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the low reactivity of NTA monomer, the monomer conversion rate of its ring-opening polymerization is low, and the polymerization reaction takes a long time. Even under the condition of adding an acid accelerator, it takes 2 to 3 days or even longer to obtain high Polypeptide products with low molecular weight, these defects lead to the preparation of polypeptides by ring-opening polymerization of NTA monomers has not been widely used
Chinese invention patent CN103289078A discloses a method for rapidly preparing polyamino acid by heating by microwave irradiation. In this method, α-amino acid-N-carboxylic acid anhydride (NCA) or α-amino acid derivative-N-carboxylic acid anhydride is prepared under low vacuum After the monomer is dissolved in the ionic liquid, the initiator is injected under the protection of an inert gas, and polyamino acid or its derivatives are synthesized by microwave irradiation heating. Although the polyamino acid prepared by this method improves the polymerization reaction rate and shortens the polymerization reaction time, but The yield of the polymerization reaction is only about 50%, which is low; and the preparation of polyamino acid by this method needs to be carried out under the protection of low vacuum environment and inert gas, the reaction conditions are harsh, and the operation is complicated and cumbersome

Method used

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  • A microwave-assisted method for preparing polypeptides
  • A microwave-assisted method for preparing polypeptides
  • A microwave-assisted method for preparing polypeptides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] S1. Preparation of S-ethoxythiolthioglycolic acid (XAA)

[0049] Sodium hydroxide (10.0g, 25.0mmol) was first dissolved in ice-cold deionized water (250mL), then chloroacetic acid (23.62g, 25.0mmol) was added and stirred to obtain a clear solution, and potassium ethyl xanthate (40.1g , 25.0mmol) was added to the above solution. The mixture was stirred at room temperature for 24 h, then it was acidified to pH=1 with 4M aqueous hydrochloric acid. The resulting cloudy mixture was extracted with chloroform (3 x 200 mL), the combined organic extracts were dried over anhydrous magnesium sulfate for 24 h, filtered and concentrated in vacuo. n-Hexane (500 mL) was then added to the oily concentrate with vigorous stirring to give an off-white solid. The solid was collected by filtration, washed with a small amount of n-hexane, and dried under vacuum at room temperature for 24 h. The obtained white solid was the final product.

[0050] S2. Preparation of N(ε)-benzyloxycarbonyl-...

Embodiment 2

[0057] S1. Preparation of S-ethoxythiolthioglycolic acid (XAA): Same as Example 1.

[0058] S2. Preparation of N(ε)-benzyloxycarbonyl-D,L-lysine-N-thiocarboxylic anhydride (Lys-NTA): Same as Example 1.

[0059] S3. Configuration of hexamethylenediamine solution: same as in Example 1.

[0060] S4. Preparation of polylysine (PLys) by microwave-assisted method

[0061] Weigh Lys-NTA (48.32mg, 0.15mmol) into a 0.2-0.5mL microwave reaction tube, add 200μL of chloroform solution to dissolve it completely, and then add initiator hexamethylenediamine solution (40.8μL, 0.001875mmol, 76.6mM ), and finally add 59.2 μL of chloroform. The molar ratio of Lys-NTA to hexamethylenediamine in the final reaction system was 80:1, and the concentration of Lys-NTA was 0.5M. The microwave reaction tube was sealed and placed in a microwave reactor with a reaction temperature of 100° C. and a reaction time of 3 h. After the reaction was completed, the reaction liquid was added dropwise into diethy...

Embodiment 3

[0063] S1. Preparation of S-ethoxythiolthioglycolic acid (XAA): Same as Example 1.

[0064] S2. Preparation of N(ε)-benzyloxycarbonyl-D, L-lysine-N-thiocarboxylic anhydride (Lys-NTA): Same as Example 1.

[0065] S3. Configuration of hexamethylenediamine solution: same as in Example 1.

[0066] S4. Preparation of polylysine (PLys) by microwave-assisted method

[0067] Weigh Lys-NTA (48.32mg, 0.15mmol) and place it in a 0.2-0.5mL microwave reaction tube, add 200μL chloroform solution to dissolve it completely, then add initiator hexamethylenediamine solution (40.8μL, 0.001875mmol, 76.6 mM), and finally add 59.2 μL of chloroform. The molar ratio of Lys-NTA to hexamethylenediamine in the final reaction system was 80:1, and the concentration of Lys-NTA was 0.5M. The microwave reaction tube was sealed and placed in a microwave reactor with a reaction temperature of 120° C. and a reaction time of 2 h. After the reaction was completed, the reaction liquid was added dropwise into d...

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Abstract

The invention discloses a microwave-assisted preparation method of polypeptide. Concrete α-amino acid-N-thiocarboxylic acid anhydride is a monomer, chloroform is used as a solvent, and hexamethylenediamine is used as an initiator, and microwave radiation is used to trigger the ring-opening polymerization of the α-amino acid-N-thiocarboxylic anhydride monomer to obtain a polymer Polypeptide material. The present invention uses the α-amino acid-N-thiocarboxylic acid anhydride monomer with good moisture and heat resistance as a raw material, and does not need harsh experimental conditions and tedious experimental operations during polymerization. Chloroform is used as a solvent and hexamethylenediamine is used as an initiator. With the assistance of microwave radiation, a polypeptide product with high monomer conversion rate and large molecular weight can be obtained in a short period of time. The invention provides a fast and efficient preparation method for the preparation of polypolypeptides, which greatly shortens the preparation time of polypolypeptides and greatly improves the conversion rate of monomers; and the experimental conditions are simple, the operation is easy, and it is easy to realize continuous scale Chemical production, with high industrial application value.

Description

technical field [0001] The present invention relates to the technical field of chemical synthesis, and more specifically, relates to a microwave-assisted preparation method of polypeptide. Background technique [0002] Microwave is a widely used electromagnetic wave, its wavelength is between 0.1-1m, and its operating frequency range is between 300MHz-300GHz. When microwaves are applied to some substances, microwaves can cause substances to absorb electromagnetic waves, and the process of materials absorbing electromagnetic waves and converting them into heat is the microwave heating process. The essence of the microwave reaction is that the dielectric material itself loses electric field energy due to the polarization of its own molecules or atoms under the action of microwaves. In the absence of microwave action, polar molecules with dipole moments are disorderly arranged due to the thermal motion of molecules, and the chances of dipole moments pointing in all directions ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/10C08G69/04
CPCC08G69/10C08G69/04
Inventor 赵天宇李培培魏聪
Owner SUN YAT SEN UNIV
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