Synthesis method of clustered peptide catalyzed by rare earth catalyst and clustered peptide synthesized by using synthesis method

A technology of rare earth catalyst and synthesis method, which is applied in the synthesis of clustering peptides and the field of synthetic clustering peptides to achieve the effects of good solubility, high catalytic activity, and cheap and easy-to-obtain raw materials

CN104059223AActive Publication Date: 2014-09-24ZHEJIANG UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2014-09-24

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Abstract

The invention discloses a synthesis method of a clustered peptide catalyzed by a rare earth catalyst. The method comprises the steps of catalyzing ring opening polymerization between N-substituted glycine-N-carboxylic acid anhydride and N-substituted glycine-N-thioanhydride by taking rare earth borohydride, alkoxyl rare earth or aryloxy rare earth as a catalyst; reacting at the temperature of 0-100 DEG C for 12h to 4d to prepare the clustered peptide with high molecular weight. The catalyst used in the synthesis method is cheap, easy to prepare and relatively high in catalytic activity; the prepared clustered peptide is high in molecular weight up to 70000, high in polymerization degree up to 1000 and narrow in molecular weight distribution range lower than 1.4.
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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 ...

Examples

Embodiment 1

[0036] Add 0.429g (3.73mmol) of N Methyl-NCA (that is, R in formula (4) is a methyl group), dissolved in 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(ethylene glycol)-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.