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Molecules 2013, 18(8), 9317-9333; doi:10.3390/molecules18089317
Article

Oligomerization of 10,16-Dihydroxyhexadecanoic Acid and Methyl 10,16-Dihydroxyhexadecanoate Catalyzed by Lipases

1, 2, 1, 1, 3, 4 and 5,*
1 Instituto Politécnico Nacional - ENCB, Carpio y Plan de Ayala S/N, Col. Casco de Santo Tomas, México, D.F., CP 11340, Mexico 2 Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana Unidad Xochimilco, Calz. del Hueso No.1100, Col. Villa Quietud, México, D.F., CP 04960, Mexico 3 CIATEJ, Av. Normalistas 800, Guadalajara, Jalisco 42270, Mexico 4 Departamento de Productos Naturales, Instituto de Química, UNAM. México, D.F. CP 04510, Mexico 5 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 / Revised: 29 July 2013 / Accepted: 30 July 2013 / Published: 5 August 2013
(This article belongs to the Section Molecular Diversity)
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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 lipases; oligomerization; natural monomer; tomato cuticle
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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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.

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