Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films

• Main Authors: Monsalve, Leandro Nicolás, Baldessari, Alicia
• Language: unknown
• Published: 2013
• Subjects: β-peptoid; Films; Lipase; Polycaprolactone; Surface properties; Argentina; Antarc*; Antarctica
• Online Access: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09598103_v_n_p_Monsalve; https://hdl.handle.net/20.500.12110/paper_09598103_v_n_p_Monsalve

The biocatalytic synthesis of a novel peptoid oligomer is reported. The oligomer is acetylated and a copolymer with polycaprolactone is prepared. These derivatives are employed for the preparation of nanoporous films. Poly[N-(2-hydroxyethyl)-β-propylamide] oligomer is synthesized using a simple enzymatic procedure involving Candida antarctica lipase B. This novel compound is obtained by a green and chemoselective method from economic reactants in good yield. The β-peptoid oligomer is characterized by spectroscopic methods showing low molecular weight and low dispersity. Two derivatives of the β-peptoid oligomer are prepared by acetylation and by grafting polycaprolactone by ring opening polymerization from the pendant hydroxyl groups. These products are blended with polycaprolactone to make films by solvent casting. The inclusion of the acyl derivatives of the β-peptoid to polycaprolactone affects the morphology of the film yielding microstructured and nanostructured patterns. © 2013 Society of Chemical Industry. Fil:Monsalve, L.N. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baldessari, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina.