Organocatalyzed Ring-Opening Polymerization of Cyclic Lysine Derivative: Sustainable Access to Cationic Poly(ε-lysine) Mimics

Abstract

Poly(ε-lysine) has broad applications and is dominantly produced via fermentation. Our group successfully realized the chemosynthesis of poly(εlysine) through ring-opening polymerization (ROP) of a 2,5-dimethylpyrroleprotected cyclic lysine monomer, but the complete removal of the protecting group suffers from a prolonged time and low yield. Herein, we have developed organocatalyzed ROP of a dimethyl-protected cyclic lysine that avoids the tedious deprotection procedures to prepare cationic poly(ε-lysine) mimics with quaternary ammonium groups in high yields. Such poly(ε-lysine) mimics not only exhibit potent antimicrobial activities but also demonstrate good biocompatibility and have no significant hemolytic activities. The antimicrobial activities of poly(εlysine) mimics were ∼80.0% at a concentration of 100 μg/mL in comparison to 76.0% of the poly(ε-lysine) control. In brief, our research provides a novel class of functional mimics of poly(ε-lysine) and opens up new avenues for designing and furnishing poly(amino acid) mimetics for biological functions and applications.

From Impossible to Possible: Atom‐Economic Polymerization of Low Strain Five‐Membered Carbonates

“…Ring‐opening polymerization (ROP) of cyclic monomers has been demonstrated as a valid way to synthesize valuable polymer materials [1–21] . The five‐membered propylene carbonate (PC) would be a desirable candidate, benefited from its wide sources (renewable CO 2 ), easy accessibility, low toxicity and broad application [22, 23] .…”

Catalyst-free aziridine-based step-growth polymerization: a facile approach to optically active poly(sulfonamide amine)s and poly(sulfonamide dithiocarbamate)s

“…Effective antimicrobial polymers have attracted much interest because of their low propensity to cause drug-resistant microorganisms. [57][58][59] Moderately hydrophobic polymers containing protonated primary or secondary/tertiary amine groups display relatively higher antimicrobial activity. 60,61 For instance, the tertiary amine covalently bonded to a polystyrene fiber exhibited high antibacterial activity against Gram-negative bacteria.…”

“…It demonstrates that this kind of polymer has the same excellent antibacterial properties as other typical polymers, such as the cationic polymers bearing quaternary ammonium or imidazolium groups. 58,59 Electrostatic interaction between the bacterial cell wall and the cationic polymer membrane may cause bacterial death. 61 Moreover, we noticed that dithiocarbamate derivatives, displaying antifungal, [63][64][65] and antibacterial activities, [66][67][68] had extensive biological applications in medicinal chemistry.…”

Antimicrobial Properties of the Triclosan-Loaded Polymeric Composite Based on Unsaturated Polyester Resin: Synthesis, Characterization and Activity

“…Antimicrobial polymers are a class of materials designed to kill or inhibit the growth of microbes on surfaces or in the environment. Polymers such as chitosan, quaternary nitrogen composites, halamines, and poly-ε-lysine may have inherent antimicrobial properties [8,9], while other polymers act as scaffolds for the immobilization of small biocides and antibiotics to enhance bactericidal activity [10][11][12]. Antimicrobial polymers currently under study include substituted or modified natural polymers, antimicrobial polymers containing multiple biocidal units attached to the backbone, polymers with a satellite terminal biocidal unit, polymer-antibiotic composite, and polymer-inorganic antimicrobial composites [13,14].…”