Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes
Polypeptide synthesis was accomplished using the urethane derivatives of amino acids as monomers, which can be easily prepared, purified, and stored at ambient temperature without the requirement for special precautions. The urethanes of amino acids are readily synthesized by the <i>N</i>...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-08-01
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| Series: | Biomedicines |
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| Online Access: | https://www.mdpi.com/2227-9059/8/9/317 |
| _version_ | 1797555156309508096 |
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| author | Takeshi Endo Atsushi Sudo |
| author_facet | Takeshi Endo Atsushi Sudo |
| author_sort | Takeshi Endo |
| collection | DOAJ |
| description | Polypeptide synthesis was accomplished using the urethane derivatives of amino acids as monomers, which can be easily prepared, purified, and stored at ambient temperature without the requirement for special precautions. The urethanes of amino acids are readily synthesized by the <i>N</i>-carbamoylation of onium salts of amino acids using diphenyl carbonate (DPC). The prepared urethanes are then efficiently cyclized to produce amino acid <i>N</i>-carboxyanhydrides (NCAs). Thereafter, in the presence of primary amines, the ring-opening polymerization (ROP) of NCAs is initiated using the amines, to yield polypeptides with controlled molecular weights. The polypeptides have propagating chains bearing reactive amino groups and initiating chain ends endowed with functional moieties that originate from the amines. Aiming to benefit from these interesting characteristics of the polypeptide synthesis using the urethanes of amino acids, various macromolecular architectures containing polypeptide components have been constructed and applied as biofunctional materials in highly efficient antifouling coatings against proteins and cells, as biosensors for specific molecules, and in targeted drug delivery. |
| first_indexed | 2024-03-10T16:43:29Z |
| format | Article |
| id | doaj.art-fce8634af0524a9a9723ff563f564e25 |
| institution | Directory Open Access Journal |
| issn | 2227-9059 |
| language | English |
| last_indexed | 2024-03-10T16:43:29Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomedicines |
| spelling | doaj.art-fce8634af0524a9a9723ff563f564e252023-11-20T11:52:04ZengMDPI AGBiomedicines2227-90592020-08-018931710.3390/biomedicines8090317Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid UrethanesTakeshi Endo0Atsushi Sudo1Molecular Engineering Institute, Kyushu Institute of Technology, Sensui-cho 1-1, Tobata-ku, Kitakyushu, Fukuoka 804-8550, JapanDepartment of Applied Chemistry, Faculty of Science and Engineering, Kindai University, Kowakae 3-4-1, Higashi Osaka, Osaka 577-8502, JapanPolypeptide synthesis was accomplished using the urethane derivatives of amino acids as monomers, which can be easily prepared, purified, and stored at ambient temperature without the requirement for special precautions. The urethanes of amino acids are readily synthesized by the <i>N</i>-carbamoylation of onium salts of amino acids using diphenyl carbonate (DPC). The prepared urethanes are then efficiently cyclized to produce amino acid <i>N</i>-carboxyanhydrides (NCAs). Thereafter, in the presence of primary amines, the ring-opening polymerization (ROP) of NCAs is initiated using the amines, to yield polypeptides with controlled molecular weights. The polypeptides have propagating chains bearing reactive amino groups and initiating chain ends endowed with functional moieties that originate from the amines. Aiming to benefit from these interesting characteristics of the polypeptide synthesis using the urethanes of amino acids, various macromolecular architectures containing polypeptide components have been constructed and applied as biofunctional materials in highly efficient antifouling coatings against proteins and cells, as biosensors for specific molecules, and in targeted drug delivery.https://www.mdpi.com/2227-9059/8/9/317amino acidspolypeptidesurethanedrug deliverybiosensors |
| spellingShingle | Takeshi Endo Atsushi Sudo Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes Biomedicines amino acids polypeptides urethane drug delivery biosensors |
| title | Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes |
| title_full | Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes |
| title_fullStr | Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes |
| title_full_unstemmed | Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes |
| title_short | Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes |
| title_sort | well defined construction of functional macromolecular architectures based on polymerization of amino acid urethanes |
| topic | amino acids polypeptides urethane drug delivery biosensors |
| url | https://www.mdpi.com/2227-9059/8/9/317 |
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