A kind of phenolic hydroxyl-containing amino acid-n-thiocarboxylic anhydride monomer and its synthesis and polymerization method

A technology of phenolic hydroxyl amino acid and thiocarboxylic anhydride is applied in the field of polymer synthesis and can solve problems such as direct synthesis of polyamino acids that have not yet been seen
CN107987032BActive Publication Date: 2020-10-30ZHEJIANG UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
ZHEJIANG UNIV
Publication Date
2020-10-30

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Abstract

The invention discloses a synthesis and polymerization method of a phenolic hydroxyl-containing amino acid-N-thiocarboxylic anhydride (NTA) monomer. An amino acid (comprising N-substituted glycine)-NTA monomer with unprotected phenolic hydroxyl is synthesized for the first time; in the synthesis method, raw materials are cheap and easy to obtain, a synthesis route is simple and the structure of atarget product is clear. In controllable ring-opening polymerization on the monomer, polymerization reaction conditions are moderate; organic amine can trigger one or more of amino acid-NTA to be subjected to the ring-opening polymerization in a solvent and react at the temperature of 0 DEGC to 150 DEG C for 0.5 hour to 4 days, so that a corresponding polyamino acid homopolymer or copolymer is prepared. A chain length of the polymer can be controlled through a feeding ratio of the monomer / an initiator and structural characteristics are clear. The invention provides a novel method for synthesizing an amino acid polymer with a side chain containing phenolic hydroxyl, and the novel method has a great application prospect in the field of biological materials.
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Description

technical field

[0001] The invention belongs to the field of polymer synthesis, and in particular relates to a synthesis and polymerization method of a phenolic hydroxyl-containing amino acid-N-thiocarboxylic anhydride (NTA) monomer. Background technique

[0002] Polyamino acids have excellent biocompatibility and degradability, and are widely used in biomedical fields, such as drug carriers and tissue engineering (J.Am.Chem.Soc.2007, 129, 5362-5363). Amino acid-N-carboxylic anhydride (N-carboxyanhydride, NCA for short) and amino acid-N-thiocarboxylic anhydride (N-thiocarboxyanhydride, NTA for short) are two common cyclic monomers for synthesizing polyamino acids. Early studies found that the hydroxyl group has nucleophilicity and can initiate the polymerization of NCA monomers (Angew. Chem., Int. Ed., 2006, 45, 5752-5784). Therefore, NCA monomers with hydroxyl groups need to protect the hydroxyl groups during synthesis and polymerization, and need to be deprotected after p...

Claims

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