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Defining Substrate Specificities for Lipase and Phospholipase Candidates
Published on: November 23, 2016
Oligomerization of 10,16-dihydroxyhexadecanoic acid and methyl 10,16-dihydroxyhexadecanoate catalyzed by lipases
M Beatriz Gómez-Patiño1, Julia Cassani, María Eugenia Jaramillo-Flores
1Instituto Politécnico Nacional-ENCB, Carpio y Plan de Ayala S/N, Col. Casco de Santo Tomas, México, D.F., CP 11340, Mexico.
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.
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