Recently, polyester syntheses through enzymatic catalysis by various monomer combinations have been extensively investigated. By utilizing specific enzymatic catalysis, enantioselective, regioselective, and chemoselective polymerizations have been developed. Worldwide potential demands for replacing petroleum derived raw materials with renewable plant-based ones in production of polymeric materials are quite significant in the social and environmental viewpoints. Tomato is one of the fruits of increased production in Mexico. However, it is still a highly perishable fruit that requires fast and efficient transportation; otherwise this factor may become a financial problem due large losses (10 to 20% of the production). Cutin is the most abundant polyester in nature and constitutes the framework of the protective cuticle of stems and leaves of higher plants. Recently, we have reported an efficient isolation of 10,16-dihydroxyhexadecanoic acid (10,16-DHPA), the main monomer of the tomato cuticle, and the preparation of some derivatives from this important cuticular component [1].<br/>Our interest in the synthesis of aliphatic polyesters is focused on the possibility to produce linear, hydroxyl functionalizable polyesters through a polymerization method that must be versatile enough to allow for the facile preparation of a variety of different materials. Thus, we are reporting the polymerization of 10,16-DHPA, and its methylated ester (methyl-10,16-dihydroxyhexadecanoate, methyl-10,16-DHHD) mediated by six different lipases. For 10,16-DHPA, optimum yields were obtained at 60⁰C using toluene and 2-methyl-2-butanol as solvent, while for methyl-10,16-DHHD the bests yields were obtained in toluene and acetonitrile. Both reactions leaded to linear polyesters according with the NMR analysis, and there was no data indicating the presence of branched polymers. Functional linear oligomers obtained from tomato agro-residual wastes, could be potentially used in the field of pharmaceutical and food industry as drug or nutraceutical carriers.<br/>[1] Arrieta-Baez, D.; Cruz-Carrillo, M.; Gómez-Patiño, M.B.; Zepeda-Vallejo, L.G. Derivatives of 10,16-Dihydroxyhexadecanoic Acid Isolated from Tomato (<i>Solanum lycopersicum</i>) as Potential Material for Aliphatic Polyesters. Molecules 2011, 16, 4923-4936.

Biopolymers from tomato agro-industrial residual wastes

249th National Meeting (2015)

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