Synthesis and characterization of amino-functional polyesters composed of lactic acids and serine amino acids

Abstract

Functional polyesters with good biocompatibility are always important biomaterials. In this study, poly (latide-co-N-trityl serine ester)s (P (LA-co-TSL)s) were synthesized through the copolymerization of lactide (LA) and N-trityl serine lactone (TSL) in toluene under 90 °C with the catalysis of diethylzinc. The molecular weight (Mn) of P (LA-co-TSL) with different TSL molar ratios (4.5%, 8.8%, 25.2%, 41.7% and 100 mol%) ranged from 3.7 kDa to 7.2 kDa with the polydipersity index (PDI) from 1.40 to 1.57. The chemical structure of poly (LA-co-TSL)s was characterized by FTIR, 1H NMR and 13C NMR spectroscopy. As the proportion of TSL in P (LA-co-TSL) increased, the glass transition temperature (Tg) of P (LA-co-TSL) increased gradually, from 56 °C of PLA to 161 °C of Poly (TSL). The initial weitht loss temperature of P (LA-co-TSL) increased as the ratio of TSL increased, from 172 °C of PLA to 230 °C of Poly (TSL). Upon removal of the N-trityl protecting group, amino functional poly (latide-co-serine ester) (P (LA-co-SL)) was realized and confirmd by FTIR and 1H NMR spectra. GPC displayed approximately 19.5% polyester backbone degradation during deprotection with trifluoroacetic acid. DSC analysis illustrated better crystallization properties of the copolyester after amino group deprotection. Using mPEG as an initiator, a new type of block copolymer, mPEG-b-poly (latide-co-N-trityl serine ester)s (mPEG-b-P (LA-co-TSL)s), was obtained. After N-trityl removal, mPEG-b-P (LA-co-TSL) displayed excellent cytocompatibility in L929 cell culture experiments.