Poly(latic acid) (PLA) is a biopolyester that has been widely employed in biomedical applications. Our research group has prepared halogenated PLA and poly(lactic acid-co-glycolic acid) (PLGA) using traditional acid-catalyzed polyesterification conditions.1 Although the chemical synthesis is very efficient, it often leaves chemical residues that have health and safety concerns.2This research initially focused on the study of enzymatic copolymerization of LA with 2-bromo-3-hydroxypropanoic acid (BrA) using Novozym 435 (immobolized CALB), which is considered an effective lipase catalyst for polyesterifications.3 However, the molecular weights of the resulting copolymers are low, which seems to be consistent with other enzymatic polymerizations of short hydroxyalkanoic acids.4 We are now investigating the effect of the length of the n-hydroxyalkanoic acids on their ability to enzymatically copolymerize with BrA. The molecular weight of enzymatically produced poly(3-hydroxypropionic acid-co-BrA) is similar to that of poly(LA-co-BrA). However, 6-hydroxyhexanoic acid and 12-hydroxydodecanoic acid produce higher molecular weight copolymers with BrA. 1H NMR spectroscopy also indicates that lactones copolymerize with BrA under enzymatic conditions.    References1. Pugh, C.; Banerjee, A.; Storms, W; Wright, C. Functional Biodegradable Polyesters UAkron 810, U.S. Patent Application 2011. 61/368413.2. Jia, H.; Wang, P. J. Biotechnol. 2007  , 132, 314-317.3. Kulshrestha, A.; Gao, W.; Gross, R.A. Macromolecules 2005  , 38, 3193-3204.4. Binns, F.; Harffey, P.; Roberts, S.M.; Taylor, A. J. Polym. Sci. Part A: Polym. Chem. 1998  , 36, 2069-2080.

Enzymatic polyesterification to produce functionalized poly(lactic acid) and poly(n-hydroxyalkanoic acid)s

246th National Meeting (2013)

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