posted on 2021-02-23, 15:10authored byJinlong Chen, Yilin Dong, Chunsheng Xiao, Youhua Tao, Xianhong Wang
Poly(ε-lysine) has broad applications and
is dominantly produced via fermentation. Our group successfully realized
the chemosynthesis of poly(ε-lysine) through ring-opening polymerization
(ROP) of a 2,5-dimethylpyrrole-protected 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(ε-lysine) 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.