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New chemosynthetic route to linear ε-poly-lysine

ε-Poly-lysine (ε-PL) is an uncommoncationic, naturally-occurring homopolymer produced by the fermentation process. Due to its significant antimicrobial activity and nontoxicity to humans, ε-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 weightof about 3 kDa. Here, we report a new chemical strategy based on ring-opening polymerization (ROP) to obtain ε-PL from lysine. The 2,5-dimethylpyrrole protected α-amino-ε-caprolactam monomer was prepared through cyclization of lysine followed by protection. ROP of this monomer, followed by the removal ofthe protecting group, 2,5-dimethylpyrrole, ultimately yielded ε-PL with varying molecular weights. The structure of this chemosynthetic ε-PL has been fully characterized by 1H NMR, 13C NMR, and MALDI-TOF MS analyses. This chemosynthetic ε-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 ε-PL on a larger-scale, facilitating the design of more advanced biomaterials.


Review on production and medical applicationsof ɛ-polylysine

ɛ-Polylysine (ɛ-PL) is a homopolyamide linked by the peptide bond between the carboxylic and epsilon amino group of adjacent lysine molecules. It is naturally occurring biodegradable and nontoxic towards human. This review article gives an insight about the various ɛ-PL producing strains, their screening procedures, mechanism of synthesis, characterization, and its application in the medical field. The polycationic nature of ɛ-PL at physiological pH makes it as one of the potential candidates in the field of drug delivery. Most of the biomedical applications till date use synthetic α-PLL as a raw material. However, it is believed that naturally occurring ɛ-PL would be an ideal substitute.


In Vitro Transfection with Plasmid DNA Using Polylysine Copolymers

SungWan Kim

Adapted from Gene Transfer: Delivery and Expression of DNA and RNA (ed. Friedmann and Rossi). CSHL Press, ColdSpring Harbor, NY, USA, 2007.


The terplex system for delivering DNA to targeted cells comprises three components—stearyl polylysine (PLL), low-densitylipoprotein (LDL), and DNA. This article describes a method for optimizing the relative amounts of these components and determining the transfection parameters for a given cell line.



                                               ICP No.11000739