Non-isocyanate urethane linkage formation using l-lysine residues as amine sources.
Amino Acids
; 51(9): 1323-1335, 2019 Sep.
Article
em En
| MEDLINE
| ID: mdl-31399841
ABSTRACT
Bio-based polyurethane materials are broadly applied in medicine as drug delivery systems. Nevertheless, their synthesis comprises the use of petroleum-based toxic amines, isocyanates and polyols, and their biocompatibility or functionalization is limited. Therefore, the use of lysine residues as amine sources to create non-isocyanate urethane (NIU) linkages was investigated. Therefore, a five-membered biscyclic carbonate (BCC) was firstly synthetized and reacted with a protected lysine, a tripeptide and a heptapeptide to confirm the urethane linkage formation with lysine moiety and to optimize reaction conditions. Afterwards, the reactions between BCC and a model protein, elastin-like protein (ELP), and ß-Lactoglobulin (BLG) obtained from whey protein, respectively, were performed. The synthesized protein materials were structural, thermally and morphologically characterized to confirm the urethane linkage formation. The results demonstrate that using both simple and more complex source of amines (lysine), urethane linkages were effectively achieved. This pioneering approach opens the possibility of using proteins to develop non-isocyanate polyurethanes (NIPUs) with tailored properties.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Poliuretanos
/
Lisina
Idioma:
En
Revista:
Amino Acids
Ano de publicação:
2019
Tipo de documento:
Article