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Synthetic method of rare earth catalyst catalyzed clustering peptide and synthesized clustering peptide

A rare earth catalyst and a synthesis method technology are applied in the field of synthetic cluster peptides and the synthesis of cluster peptides to achieve the effects of stable properties, simple and easy synthesis process, and large-scale industrial production.

Active Publication Date: 2016-06-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method of synthesizing clustered peptides with rare earth catalysts has not been reported yet

Method used

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  • Synthetic method of rare earth catalyst catalyzed clustering peptide and synthesized clustering peptide
  • Synthetic method of rare earth catalyst catalyzed clustering peptide and synthesized clustering peptide
  • Synthetic method of rare earth catalyst catalyzed clustering peptide and synthesized clustering peptide

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Experimental program
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Effect test

Embodiment 1

[0036] Add 0.429g (3.73mmol) of N Methyl-NCA (that is, R in formula (4) is methyl), dissolved with 7.5mL N,N-dimethylformamide (DMF), and then added 0.17mLDy (BH 4 ) 3 THF solution (0.022mol / L, 0.00374mmol), N Methyl-NCA and Dy(BH 4 ) 3 The molar ratio is 1000:1, sealed and placed in a 40°C oil bath to react for 4 days. After the reaction, the mixture is poured into ether to precipitate and filtered, and the obtained polymer is vacuum-dried for 4 days to obtain a clustered peptide. The yield 99%. The SEC number-average absolute molecular weight of the obtained polymer was 74.1 kDa, and the molecular weight distribution was 1.42.

Embodiment 2

[0038] Other polymerization conditions are identical with embodiment 1, difference is to use Sc(BH 4 ) 3 Initiate for the initiator N Allyl-NCA (that is, R in the formula (4) is allyl) ring-opening polymerization, the solvent is benzonitrile, N Allyl-NCA and Sc(BH 4 ) 3 The molar ratio was 400:1, and the reaction was carried out in a constant temperature bath at 80° C. for 24 hours, and the yield of the obtained clustered peptide was 92%. The SEC number-average absolute molecular weight of the obtained polymer was 39.0 kDa, and the molecular weight distribution was 1.36.

Embodiment 3

[0040] Other polymerization conditions are identical with embodiment 1, difference is with Nd (BH 4 ) 3 Initiate for the initiator N Oligo(ethyleneglycol)-NCA (that is, R in formula (4) is an oligoethylene glycol group, repeating unit=4), ring-opening polymerization, the solvent is N-methylpyrrolidone (NMP), N Oligo(ethyleneglycol)-NCA and Nd(BH 4 ) 3 The molar ratio was 50:1, and the reaction was carried out in a constant temperature bath at 0°C for 2 days, and the yield of the obtained clustered peptide was 98%. The SEC number-average absolute molecular weight of the obtained polymer was 12.5 kDa, and the molecular weight distribution was 1.19.

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Abstract

The invention discloses a method for synthesizing clustered peptides catalyzed by a rare earth catalyst. In the method, rare earth borohydride, alkoxy rare earth or aryloxy rare earth are used as catalysts to catalyze N-substituted glycine-N-carboxylic acid anhydride and N-substituted glycine - Ring-opening polymerization of N-thiocarboxylic acid anhydride, reacting at a temperature of 0°C to 100°C for 12 hours to 4 days to prepare high molecular weight clustered peptides. The catalyst used in the invention is cheap and easy to prepare, has high catalytic activity, and the prepared polymerized peptide has a high molecular weight of up to 70,000, a high degree of polymerization of up to 1000, and a narrow molecular weight distribution of less than 1.4.

Description

technical field [0001] The invention belongs to the field of polymer synthesis, and in particular relates to a method for synthesizing a clustering peptide catalyzed by a rare earth catalyst and the synthesized clustering peptide. Background technique [0002] Clustered peptides are a class of biomaterials that have a similar structure to polypeptides. The main chain structure is polyglycine, and the nitrogen atoms contain natural or synthetic substituents. Because of the substituents on the nitrogen atoms, there are no hydrogen-bonding interactions in the backbone of the polypeptide, a property that allows it to have good solubility in most organic solvents and can withstand thermal processing. Although lacking hydrogen-bonding interactions, clustered peptides can still form stable secondary structures through the steric hindrance and electronic properties of side groups. Compared with polypeptide materials, polypeptides have better membrane permeability and resistance to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/16C08G69/42
Inventor 凌君陶鑫峰邓扬威沈之荃
Owner ZHEJIANG UNIV
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