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Novel cyclic peptide containing 2-methyl-3-aminobenzoic acid

A technology of aminobenzoic acid and amino acid, applied in the field of nanotubes, can solve problems such as unreported

Inactive Publication Date: 2015-04-29
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Cyclic peptides composed of all nonpolar amino acids modified by 2-methyl-3-aminobenzoic acid (γ-Mba) have not been reported so far

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1 Synthesis of 3-(9-fluorenylmethoxycarbonyl)amino-2-methylbenzoic acid (Fmoc-γ-Mba)

[0023] Dissolve γ-Mba (1mmol, 0.15116g) in distilled water, Na 2 CO 3 (1mmol, 0.106g) was slowly added thereto until all of the γ-Mba was dissolved; 9-fluorenylmethylsuccinimidyl carbonate (Fmoc-OSu, 1.05mmol, 0.3542g) was dissolved in 5ml 1,4-dioxane and slowly added dropwise to it, reacted overnight in ice bath for 1 hour; after the reaction, dilute with distilled water, extract the solution with ethyl acetate, and collect the lower water layer; adjust the pH of the water layer to pH=1 with HCl; Then extract the aqueous layer with ethyl acetate, collect the upper organic layer; evaporate the organic solvent to obtain the product Fmoc-γ-Mba, MS collection of spectra ( figure 2 ) to confirm its generation.

Embodiment 2

[0024] Example 2 Solid phase synthesis of cyclohexapeptide [cyclo-(L-Phe-γ-Mba-L-Phe-D-Phe-L-Phe-D-Phe)]

[0025] (1) Trityl chloride resin (TCR, 1.66mmol, 0.830g) was swollen with 8ml of dichloromethane (DCM) for 45min, and the solvent was removed by vacuum; then Fmoc-L-Phe (2.49mmol, 0.964g) and N, N-diisopropylethylamine (DIEA, 2.49mmol, 0.434ml) were dissolved in 10ml of dichloromethane and then added to the above resin, stirred and reacted at room temperature for 4h; (DCM / MeOH / DIEA=8 / 2 / 1, volume ratio) was capped, washed with DCM and anhydrous ether respectively, and finally vacuum-dried at 35° C. for 12 h.

[0026] (2) The resin (0.72 mmol, 1.6 g) dried in the previous step was swelled with 20 ml of DCM for 45 min, and the solvent was removed.

[0027] (3) The resin was washed with N,N-dimethylformamide (DMF), deprotected with 20% piperidine (PIP) in DMF, washed with DMF, and the solvent was removed.

[0028] (4) Fmoc-γ-Mba (3.96mmol, 1.476g) and 1-hydroxybenzotriazole...

Embodiment 3

[0036] Example 3 Cyclic hexapeptide self-assembled nanotubes

[0037] Accurately weigh 1mg of the above-mentioned cyclic hexapeptide, add 1ml of DCM, ultrasonically disperse, and let the cyclic hexapeptide self-assemble at room temperature for 2-96 hours. 35°C, 12h, the cyclohexapeptide self-assembled nanotubes were obtained, Figure 4 is its infrared spectrum.

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Abstract

The invention relates to a novel cyclic peptide containing 2-methyl-3-aminobenzoic acid (gamma-Mba). The cyclic peptide contains at least one 2-methyl-3-aminobenzoic acid (gamma-Mba) and 3-31 nonpolar amino acids, wherein the nonpolar amino acids are L- or D- alpha-amino acids and are any one or more of 8 natural nonpolar amino acids. The cyclic peptide can be assembled into nanotubes, so as to be used as medicament carriers, membrane channels, biosensors and the like.

Description

technical field [0001] The invention relates to a novel cyclic peptide containing 2-methyl-3 aminobenzoic acid (γ-Mba) and nanotubes formed by self-assembly. Background technique [0002] Nanotechnology has become one of the most important research fields and development frontiers in modern science. Nanotechnology has a wide range of applications in industrial manufacturing, national defense construction, medical technology, optical devices, microstructures, and microelectronics. Among all kinds of nanomaterials, nanotubes whose size is in the molecular range, because of their special shape and properties, are widely used in the fields of chemistry, biochemistry and material science including catalysis, separation, optoelectronic materials and drug delivery. Both have potential and broad application value. Among them, organic nanotubes formed by self-assembly of polypeptides are particularly attractive. [0003] The tubular structure formed by polypeptides has precedents i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/56B82Y5/00B82Y15/00
Inventor 栾立标王冬梅
Owner CHINA PHARM UNIV
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