TY - JOUR
T1 - Oligomerization of 10,16-dihydroxyhexadecanoic acid and methyl 10,16-dihydroxyhexadecanoate catalyzed by lipases
AU - Gómez-Patiño, M. Beatriz
AU - Cassani, Julia
AU - Jaramillo-Flores, María Eugenia
AU - Zepeda-Vallejo, L. Gerardo
AU - Sandoval, Georgina
AU - Jimenez-Estrada, Manuel
AU - Arrieta-Baez, Daniel
PY - 2013/8
Y1 - 2013/8
N2 - 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.
AB - 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.
KW - Lipases
KW - Natural monomer
KW - Oligomerization
KW - Tomato cuticle
UR - http://www.scopus.com/inward/record.url?scp=84883175307&partnerID=8YFLogxK
U2 - 10.3390/molecules18089317
DO - 10.3390/molecules18089317
M3 - Artículo
SN - 1420-3049
VL - 18
SP - 9317
EP - 9333
JO - Molecules
JF - Molecules
IS - 8
ER -