Biodegradable poly(anhydrides) are widely used as controlled drug systems because they hydrolyze to diacid monomers  in vivo.  There is a continued interest to develop biocompatible materials that are stable, show low toxicity and can erode at different rates. In this study we approached the synthesis of a biocompatible poly(anhydride) based on the structure of a natural metabolite; 4-hydroxyphenylpyruvic acid (4-HPPA) was selected because it is an intermediate in the metabolism of phenylalanine. Here, we report the synthesis of 4,4'-oxydiphenylpyruvic acid that has the dual functionality for conversion to a polymer. 4-Hydroxybenzaldehyde was reacted with 4-fluorobenzaldehye to give a bis-aldehyde, which upon reaction with N-acetyl glycine lead to a cyclic intermediate. Hydrolysis of the cyclic intermediate was successfully carried out to give 4,4'-oxydiphenylpyruvic acid. The products were characterized by 1H and 13C NMR spectroscopy, infrared spectroscopy, and gas-chromatography/mass spectrometry.

Synthesis of a phenylpyruvate-based biodegradable polymer

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.