Polymers derived from the amino acid L-tyrosine: polycarbonates, polyarylates and copolymers with poly(ethylene glycol)

Abstract

The natural amino acid L-tyrosine is a major nutrient having a phenolic hydroxyl group. This feature makes it possible to use derivatives of tyrosine dipeptide as a motif to generate diphenolic monomers, which are important building blocks for the design of biodegradable polymers. Particularly useful monomers are desaminotyrosyl-tyrosine alkyl esters (abbreviated as DTR, where R stands for the specific alkyl ester used). Using this approach, a wide variety of polymers have been synthesized. Here, tyrosine-derived polycarbonates, polyarylates, and polyethers are reviewed with special emphasis on recent developments relating to cellular and in vivo responses, sterilization techniques, surface characterization, drug delivery, and processing and fabrication techniques. The commercial development of tyrosine-derived polycarbonates is most advanced, with one polymer, poly(DTE carbonate) (E=ethyl), being under review by the USA Federal Drug Administration.