Preparation of poly(serine ester)s by ring-opening polymerization of N-trityl serine lactone under catalysis of ZnEt₂

Abstract

Poly(N-trityl serine lactone)(PTSL) and mPEG-block-poly(N-trityl serine lactone)(mPEG-b-PTSL, PEG=polyethylene glycol) were synthesized via the ring-opening polymerization of N-trityl serine lactone(TSL) with diethyl zinc(ZnEt₂) as catalyst. The structures of these polymers were confirmed with hydrogen nuclear magnetic resonance(¹H NMR) spectroscopy, carbon nuclear magnetic resonance(¹³C NMR) spectroscopy and infrared(IR) spectrometer. The thermal decomposition temperature and glass transition temperature of PTSL were 241 and 161 °C, respectively. A series of mPEG-b-PTSL with different molecular weights(M _n’s from 7000 to 32000) was obtained by tuning the TSL/mPEG feed ratio. After the removal of the trityl groups, mPEG-block-poly(serine lactone)(mPEG-b-PSL) was obtained as a new kind of cationic block copolymer. Low cytotoxicity of these polymers to L929 cells was confirmed via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide(MTT) assay.

Keywords

Diethyl zinc catalyst / Poly(serine lactone) / Pseudopoly(amino acid) / Ring-opening polymerization / Diethyl zinc(ZnEt₂)

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