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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,*
Received: 16 July 2013; in revised form: 29 July 2013 / Accepted: 30 July 2013 / Published: 5 August 2013
(This article belongs to the Section Organic Synthesis)
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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


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