Antimicrobial peptide synthesis method with all amino acids being D-type amino acids

A synthetic method, amino acid technology, applied in the field of chemistry, which can solve problems such as limited research and application

Active Publication Date: 2018-10-09
OCEAN UNIV OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Tachyplesin I is an antimicrobial peptide with broad-spectrum antibacterial activity, but its research and application are limited due to its hemolytic problem

Method used

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  • Antimicrobial peptide synthesis method with all amino acids being D-type amino acids
  • Antimicrobial peptide synthesis method with all amino acids being D-type amino acids
  • Antimicrobial peptide synthesis method with all amino acids being D-type amino acids

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Embodiment Construction

[0017] The present invention will be described in detail below in combination with specific embodiments. Such as figure 1 Shown, synthetic method of the present invention is as follows:

[0018] 1. Synthesis of D-type Tachyplesin I (TPAD): select Rink-Amide resin, activate the resin with 1:1 dichloromethane and N,N-dimethylformamide, and then follow the solid-phase synthesis method to obtain a linear Peptide KWCFRVCYRGICYRRCR*, in which all 17 amino acids use D-type amino acids.

[0019] 2. Then use a 20mL mixed solution of trifluoroacetic acid (TFA): water: phenol: triisopropylsilane = 88:5:5:2 to cut the resin, remove the trifluoroacetic acid by rotary evaporation, add glacial ether, white The solid is precipitated, and the centrifuged solid is dissolved in water, and freeze-dried using a freeze dryer to obtain a solid powder.

[0020] 3. Then start to build two pairs of disulfide bonds. The sulfhydryl protecting group selected for the 3-position and 16-position cysteine ...

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Abstract

The invention discloses an antimicrobial peptide synthesis method with all amino acids being D-type amino acids. The method comprises the following steps: activating resin with dichloromethane and N,N-dimethylformamide, and obtaining a straight-chain peptide KWCFRVCYRGICYRRCR* by a solid-phase synthesis method; cutting the resin with a mixed solution of trifluoroacetic acid, water, phenol and triisopropylsilane, performing rotary evaporation to remove the trifluoroacetic acid, adding frozen diethyl ether to precipitate a white solid, and performing freeze drying with a freezer drier to obtainsolid powder; constructing two pairs of disulfide bonds, wherein mercapto protective groups selected by 3-site,16-site cysteine are triphenylmethyl, mercapto protective groups selected by 7-site, 12-site cysteine are acetamide methyl. The method has the beneficial effect that the hemolytic activity is significantly reduced on the basis of maintaining the original antimicrobial activity.

Description

technical field [0001] The invention belongs to the technical field of chemistry and relates to a method for synthesizing antibacterial peptides in which all amino acids are D-type amino acids. Background technique [0002] Tachyplesin I is an antimicrobial peptide with broad-spectrum antibacterial activity, but its research and application are limited due to its hemolytic problem. Studies have shown that applying D-amino acids to polypeptides can improve their stability. Therefore, such modifications to the original polypeptide may enhance its biological activity. [0003] Considering that the D-type isoleucine is expensive, the isoleucine in the wild-type polypeptide (KWCFRVCYRGICYRRCR*) sequence is replaced by leucine, so the newly designed polypeptide sequence is KWCFRVCYRGLCYRRCR*. Contents of the invention [0004] The object of the present invention is to provide a method for synthesizing antibacterial peptides in which all amino acids are D-type amino acids. The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/08C07K1/04C07K1/06
CPCC07K7/08Y02P20/55
Inventor 于日磊史娟江涛
Owner OCEAN UNIV OF CHINA
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