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Synthesis of amphipathic block antibacterial peptide as well as preparation method and application of assembly of amphipathic block antibacterial peptide

An amphiphilic block and antimicrobial peptide technology, which is applied in the field of synthesis and assembly preparation, can solve the problems of unsatisfactory antibacterial effect, poor biocompatibility, limitations, etc., and achieve wide application prospects and value. control, low cost effect

Inactive Publication Date: 2017-05-31
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although inorganic antibacterial agents such as Ag and its metal oxides have good antibacterial properties, their biocompatibility limits their wide application in the human body; while organic antibacterial agents such as quaternary ammonium salts, halogenated amines, and biguanides And chitosan, etc., but also because of poor biocompatibility or unsatisfactory antibacterial effect and other defects limit its application

Method used

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  • Synthesis of amphipathic block antibacterial peptide as well as preparation method and application of assembly of amphipathic block antibacterial peptide
  • Synthesis of amphipathic block antibacterial peptide as well as preparation method and application of assembly of amphipathic block antibacterial peptide
  • Synthesis of amphipathic block antibacterial peptide as well as preparation method and application of assembly of amphipathic block antibacterial peptide

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preparation example Construction

[0075]

[0076] A preparation method of the above-mentioned amphiphilic block antimicrobial peptide, which comprises the steps of:

[0077] (1), react the hydrophilic amino acid containing the amino protecting group and triphosgene in an organic solvent to obtain a hydrophilic amino acid-N-carboxyl-α-amino acid anhydride monomer, and combine the hydrophobic amino acid and triphosgene in an organic solvent Reaction in solvent to obtain hydrophobic amino acid-N-carboxyl-α-amino acid anhydride monomer;

[0078] (2), mix 0.200-1.000mmol initiator and 0.200-100.000mmol hydrophilic amino acid-N-carboxyl-α-amino acid anhydride monomer in 20-50mL organic solvent, and react under vacuum to obtain:

[0079] Wherein A represents an initiator, and Z' represents an amino protecting group;

[0080] (3), continue to add hydrophobic amino acid-N-carboxyl-α-amino acid anhydride monomer and react under vacuum to obtain:

[0081]

[0082] (4), repeat steps (2) and (3) n-1 times, obtain ...

Embodiment 1

[0129] The first step: preparation method of amphiphilic diblock antimicrobial peptide

[0130] The preparation method of the amphiphilic diblock antimicrobial peptide of the present embodiment, it comprises the steps:

[0131] (1) 30.000g (107.14mmol) benzyloxycarbonyl‐lysine and 13.790g (46.43mmol) triphosgene were subjected to a nucleophilic reaction in 40mLDMF at a temperature of 40°C for 3h to obtain Z'‐Lys‐NCA Monomer (Z' represents the benzyloxycarbonyl protecting group), 30.000g (181.18mmol) of phenylalanine and 23.400g (78.78mmol) of triphosgene in 40mL of DMF through nucleophilic reaction, the temperature is 40 ° C, the time is 3h, Obtain Phe-NCA monomer;

[0132] (2), 0.022mL (0.217mmol) isobutylamine (as an initiator) and 2.000g (6.540mmol) Z'‐Lys‐NCA monomer (Z' represents the benzyloxycarbonyl protecting group) was dissolved in 20mL (260mmol) Carry out ring-opening polymerization in DMF, react under vacuum for 12 hours at a temperature of 50°C, and obtain a hyd...

Embodiment 2

[0160] The first step: preparation method of amphiphilic diblock antimicrobial peptide

[0161] The preparation method of the amphiphilic diblock antimicrobial peptide of the present embodiment, it comprises the steps:

[0162] (1) 30.000g (107.14mmol) benzyloxycarbonyl‐lysine and 13.790g (46.43mmol) triphosgene were subjected to a nucleophilic reaction in 40mL DMF at a temperature of 40°C for 3 hours to obtain Z'‐Lys‐ NCA monomer (Z' represents the benzyloxycarbonyl protecting group), 30.000g (181.18mmol) of phenylalanine and 23.400g (78.78mmol) of triphosgene in 40mL of DMF by nucleophilic reaction, the temperature is 40 ℃, the time is 3h , to obtain the Phe-NCA monomer;

[0163] (2), 0.022mL (0.217mmol) isobutylamine (as an initiator) and 2.000g (6.540mmol) Z'‐Lys‐NCA monomer (Z' represents the benzyloxycarbonyl protecting group) were dissolved in 20mL DMF for development Ring polymerization, reacting under vacuum for 12 hours at a temperature of 50°C to obtain a hydrophi...

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Abstract

The invention provides synthesis of amphipathic block antibacterial peptide as well as a preparation method and application of an assembly of the amphipathic block antibacterial peptide. The amphipathic block antibacterial peptide is prepared from hydrophilic amino acid, hydrophobic amino acid, triphosgene, an organic solvent, an initiator, a de-protection agent and a precipitant. The amphipathic block antibacterial peptide provided by the invention has broad-spectrum and excellent antibacterial properties, is an economic, low-toxic and stable biological material, has wide application prospects and values, is low in raw material price, easy in raw material obtaining and low in cost, and in addition, the synthesis is simple in route and controllable in condition.

Description

technical field [0001] The invention belongs to the field of antibacterial biomaterials, and in particular relates to the synthesis of an amphiphilic block antibacterial peptide and the preparation method and application of an assembly thereof. Background technique [0002] At present, the long-term abuse of antibiotics has led to the emergence and widespread spread of super-resistant bacteria, which has reduced the effectiveness of antibiotics, and even some bacteria are difficult to kill by antibiotics, such as bacteria carrying the MCR‐1 gene. Therefore, it is urgent to seek new antibacterial agents to replace traditional antibiotics. Although inorganic antibacterial agents such as Ag and its metal oxides have good antibacterial properties, their biocompatibility limits their wide application in the human body; while organic antibacterial agents such as quaternary ammonium salts, halogenated amines, and biguanides And chitosan, etc., also limit its application because of...

Claims

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Application Information

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IPC IPC(8): C08G69/08A61K47/34B01J19/00
CPCA61K47/34B01J19/0093C08G69/08
Inventor 苏小凯周春才
Owner TONGJI UNIV
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