Poly(triol α-ketoglutarate) as biodegradable, chemoselective, and mechanically tunable elastomers

We report the design of several elastomers based on the thermal polycondensation of alpha-ketoglutaric acid and one of three triols: glycerol, 1,2,4-butanetriol, or 1,2,6-hexanetriol. By varying the curing temperature and the duration of the curing process, a wide range of mechanical properties was achieved. The values of the Young's modulus (0.1 - 657.4 MPa), ultimate stress (0.2 - 30.8 MPa), and ultimate strain (22 - 583%) encompass the mechanical properties of many biological materials, increasing the probability of success for the use of poly(triol alpha-ketoglutarate) as a biomaterial. Furthermore, the poly(triol alpha-ketoglutarate) series hydrolytically degraded in as fast as 2 days and as long as 28 days in phosphate-buffered saline solutions. For postpolymerization modifications, the repeat units contain ketones, which are capable of reacting with a variety of oxyamine--terminated molecules to generate stable oxime linkages. Finally, the versatility and utility of these elastomers were demonstrated by creating micropatterned structures and films for biospecific cell scaffold supports.