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Facile synthesis of polymethionine oxides through polycondensation of activated urethane derivative of α-amino acid and their application to antifouling polymer against proteins and cellsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4py01656d
We have developed a facile route for the synthesis of poly(methionine) and poly(methionine oxide), including poly(methionine sulfoxide), and poly(methionine sulfone) through polycondensation of the corresponding N -phenoxycarbonyl derivatives of α-amino acids in the presence of amines. These urethan...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Online Access: | Get full text |
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| Summary: | We have developed a facile route for the synthesis of poly(methionine) and poly(methionine oxide), including poly(methionine sulfoxide), and poly(methionine sulfone) through polycondensation of the corresponding
N
-phenoxycarbonyl derivatives of α-amino acids in the presence of amines. These urethane derivatives were readily synthesized through N-carbamylation of onium salt of methionine with diphenyl carbonate. Oxidation of sulfide on the urethane derivative with a hydrogen peroxide selectively provided the corresponding sulfoxide and sulfone in high yield. Heating of their urethane derivative 60 °C successfully obtained the corresponding polypeptide through polycondensation accompanying the elimination of phenol and CO
2
in high yield. The molecular weight of polypeptide was adjusted by varying the feed ratio of urethane derivative to amine. MALDI-TOF mass analysis revealed that the added amine was successfully incorporated into the terminal end of the polypeptide. Taking advantage of our facile synthetic route to synthesize a polypeptide, we have synthesized a polystyrenes bearing oligo(
l
-methionine sulfoxide) in the side chain, and investigated their application as a surface-coating polymer that leads to antifouling property against proteins and cells. The polystyrene was readily synthesized through polycondensation of a urethane derivative of
l
-methionine sulfoxide in the presence of 4-vinylbenzylamine, followed by radical polymerization with water-soluble azo initiator. The inhibition of protein (hRP-IgG) adsorption and F9 cells adhesion was observed on the surface of the polymer-coated PS plate because of the hydrophilic nature of
l
-methionine sulfoxide segment. In addition, the result of CCK-8 assay reveals a low cytotoxicity against F9 cells, indicating that the polymer possesses a high biocompatibility.
Polymethionine(oxide)s were readily synthesized through polycondensation with amines, accompanying the elimination of phenol and CO
2
and used as antifouling polymer against biological matters. |
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| ISSN: | 1759-9954 1759-9962 |
| DOI: | 10.1039/c4py01656d |