One-Pot Synthesis of Amino Acid-Based Polyelectrolytes and Nanoparticle Synthesis
| Autor: | Stefan Mommer, Martin Möller, Helmut Keul |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Polymers and Plastics
Epoxide Bioengineering 02 engineering and technology 010402 general chemistry 01 natural sciences Caproic Acid Biomaterials chemistry.chemical_compound Polymer chemistry Materials Chemistry Thiolactone Peptide bond Amino Acids Alanine chemistry.chemical_classification Dipeptide Chemistry 021001 nanoscience & nanotechnology Polyelectrolytes 0104 chemical sciences Amino acid Solutions Monomer Nanoparticles 0210 nano-technology |
| Zdroj: | Biomacromolecules. 18(1) |
| ISSN: | 1526-4602 |
| Popis: | In this manuscript, a biscyclic monomer with an epoxide and a thiolactone ring connected by a urethane bond is used for the synthesis of amino acid-functional polyelectrolytes. In a first step, lithium salts of amino acids react selectively with the thiolactone ring by ring-opening, formation of an amide bond, and a thiol group. In a second step and in the presence of a base a polymeric building block is formed by polyaddition of the thiolate to the epoxide ring. The reaction occurs at room temperature in water as solvent. The resulting polymeric building block has a poly(thioether urethane) backbone, with hydroxyl- and amino acid side groups; the connection of the amino acid to the backbone occurs by an amide bond. As proof of concept, a selected series of amino acids and derivatives of such is used: glycine, alanine, tyrosine, glutamic acid, ε-amino caproic acid (as a lysine surrogate), BOC-lysine-O-methyl ester, BOC-lysine, and the dipeptide carnosine. The resulting polymer building blocks with molecular weights of M |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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