New bio-renewable polyester with rich side amino groups from l-lysine via controlled ring-opening polymerization

Abstract

Lysine, a renewable resource from biomass fermentation, was converted to pure O-carboxyanhydride monomer, then well-defined polyester with amino groups was prepared via controlled ring-opening polymerization.

Controlled Ring‐Opening Polymerization of O‐Carboxyanhydrides Using a β‐Diiminate Zinc Catalyst

“…While these issues can be addressed through the ROPo f functional LA derivatives,s uch as hydroxy- [2] and norbornene-lactide, [3] these monomers require multistep synthesis, and the ROPl acks control. [10] OCAs thus provide significant potential for building complex PA HA structures for various applications including drug delivery, [6,9b, 11] gene delivery, [9a] and tissue engineering. [10] OCAs thus provide significant potential for building complex PA HA structures for various applications including drug delivery, [6,9b, 11] gene delivery, [9a] and tissue engineering.…”

One-pot atom-efficient synthesis of bio-renewable polyesters and cyclic carbonates through tandem catalysis

“…ROP of OCA, by releasing a molecule of CO 2 , is able to generate side-chainfunctionalized polyesters effectively. 10 12 We recently develop a strategy to synthesize a new OCA monomer (lysine-OCA) and amino-functionalized renewable polyester from an abundant low-cost natural resource: lysine, and the resultant lysine-based polyester showed excellent cell compatibility. 10 Although significant successes were accomplished for the polymerization of OCAs, use of easily accessible catalysts that exhibit high activities and high atom efficiency, have not been reported.…”

“…10 12 We recently develop a strategy to synthesize a new OCA monomer (lysine-OCA) and amino-functionalized renewable polyester from an abundant low-cost natural resource: lysine, and the resultant lysine-based polyester showed excellent cell compatibility. 10 Although significant successes were accomplished for the polymerization of OCAs, use of easily accessible catalysts that exhibit high activities and high atom efficiency, have not been reported. To suppress unwanted CO 2 release, the attempt to develop a single tandem catalyst to connect two independent catalytic cycles for the production of polyesters and the formation of cyclic carbonates from CO 2 and epoxide has attracted our interest (Scheme 1).…”

Poly(hydroxy acid) Nanoparticles for the Encapsulation and Controlled Release of Doxorubicin

“…N ‐Carbobenzyloxy‐ l ‐lysine (Lys(Cbz)) and γ‐benzyl‐ l ‐glutamate (Glu(Bz)) were selected to independently provide hydrophilic ester repeat units following polyester deprotection. The ROP of carboxyanhydride monomers may be initiated from the hydroxyl functional groups of small molecules or macromolecules . Here, isobutanol was selected to initiate the ROP of the Phe OCA to generate a hydrophobic poly(PheLA) (LA = lactic acid) macromolecule ( Scheme ).…”