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Oligomerization of 10,16-Dihydroxyhexadecanoic Acid and Methyl 10,16-Dihydroxyhexadecanoate Catalyzed by Lipases
Instituto Politécnico Nacional - ENCB, Carpio y Plan de Ayala S/N, Col. Casco de Santo Tomas, México, D.F., CP 11340, Mexico
Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana Unidad Xochimilco, Calz. del Hueso No.1100, Col. Villa Quietud, México, D.F., CP 04960, Mexico
CIATEJ, Av. Normalistas 800, Guadalajara, Jalisco 42270, Mexico
Departamento de Productos Naturales, Instituto de Química, UNAM. México, D.F. CP 04510, Mexico
Instituto Politécnico Nacional - CNMN, Calle Luis Enrique Erro s/n, Unidad Profesional Adolfo López Mateos, Col. Zacatenco, México D.F., CP 07738, Mexico
* Author to whom correspondence should be addressed.
Received: 16 July 2013; in revised form: 29 July 2013 / Accepted: 30 July 2013 / Published: 5 August 2013
Abstract: The main monomer of tomato cuticle, 10,16-dihydroxyhexadecanoic acid (10,16-DHPA) and its methyl ester derivative (methyl-10,16-dihydroxyhexadecanote; methyl-10,16-DHHD), were used to study their oligomerization reactions catalyzed by five lipases: Candida antarctica lipase B (CAL-B), Rhizomucor miehei lipase (RM), Thermomyces lanuginosus lipase (TL), Pseudomonas cepacia lipase (PCL) and porcine pancreatic lipase (PPL). For 10,16-DHPA, optimum yields were obtained at 60 °C using toluene and 2-methyl-2-butanol (2M2B) as solvent, while for methyl-10,16-DHHD the bests yields were obtained in toluene and acetonitrile. Both reactions leaded to linear polyesters according to the NMR and FT-IR analysis, and there was no data indicating the presence of branched polymers. Using optimized conditions, poly(10,16-DHPA) and poly(methyl-10,16-DHHD) with Mw = 814 and Mn = 1,206 Da, and Mw = 982 and Mn = 860 Da, respectively, were formed according to their MALDI-TOF MS and ESI-MS data. The self-assembly of the polyesters obtained were analyzed by AFM.
Keywords: lipases; oligomerization; natural monomer; tomato cuticle
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Gómez-Patiño, M.B.; Cassani, J.; Jaramillo-Flores, M.E.; Zepeda-Vallejo, L.G.; Sandoval, G.; Jimenez-Estrada, M.; Arrieta-Baez, D. Oligomerization of 10,16-Dihydroxyhexadecanoic Acid and Methyl 10,16-Dihydroxyhexadecanoate Catalyzed by Lipases. Molecules 2013, 18, 9317-9333.
Gómez-Patiño MB, Cassani J, Jaramillo-Flores ME, Zepeda-Vallejo LG, Sandoval G, Jimenez-Estrada M, Arrieta-Baez D. Oligomerization of 10,16-Dihydroxyhexadecanoic Acid and Methyl 10,16-Dihydroxyhexadecanoate Catalyzed by Lipases. Molecules. 2013; 18(8):9317-9333.
Gómez-Patiño, M. Beatriz; Cassani, Julia; Jaramillo-Flores, María E.; Zepeda-Vallejo, L. Gerardo; Sandoval, Georgina; Jimenez-Estrada, Manuel; Arrieta-Baez, Daniel. 2013. "Oligomerization of 10,16-Dihydroxyhexadecanoic Acid and Methyl 10,16-Dihydroxyhexadecanoate Catalyzed by Lipases." Molecules 18, no. 8: 9317-9333.