New chemosynthetic route to linear ?-poly-lysine.

ABSTRACT: ?-Poly-lysine (?-PL) is an uncommon cationic, naturally-occurring homopolymer produced by the fermentation process. Due to its significant antimicrobial activity and nontoxicity to humans, ?-PL is now industrially produced as an additive, e.g. for food and cosmetics. However, the biosynthetic route can only make polymers with a molecular weight of about 3 kDa. Here, we report a new chemical strategy based on ring-opening polymerization (ROP) to obtain ?-PL from lysine. The 2,5-dimethylpyrrole protected ?-amino-?-caprolactam monomer was prepared through cyclization of lysine followed by protection. ROP of this monomer, followed by the removal of the protecting group, 2,5-dimethylpyrrole, ultimately yielded ?-PL with varying molecular weights. The structure of this chemosynthetic ?-PL has been fully characterized by 1H NMR, 13C NMR, and MALDI-TOF MS analyses. This chemosynthetic ?-PL exhibited a similar pKa value and low cytotoxicity as the biosynthetic analogue. Using this new chemical strategy involving ROP without the need for phosgene may enable a more cost effective production of ?-PL on a larger-scale, facilitating the design of more advanced biomaterials.

SUBMITTER: Tao Y 

PROVIDER: S-EPMC6054053 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature