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

M Beatriz Gómez-Patiño,Daniel Arrieta-Baez,Georgina Sandoval,L Gerardo Zepeda-Vallejo,Julia Cassani,Manuel Jimenez-Estrada,María Jaramillo-Flores

doi:10.3390/molecules18089317

M Beatriz Gómez-Patiño, Daniel Arrieta-Baez + Show 5 more

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https://doi.org/10.3390/molecules18089317

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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.

Highlights

IntroductionThe synthesis of aliphatic polyesters continues to be of significant interest in biomedical applications (drug delivery systems, wound closure and healing products, and surgical implant devices) [1,2,3] and some applications that include food containers, soil retention sheeting, agriculture film, waste bags and the use as a packaging material in general [4]
The synthesis of aliphatic polyesters continues to be of significant interest in biomedical applications [1,2,3] and some applications that include food containers, soil retention sheeting, agriculture film, waste bags and the use as a packaging material in general [4]
Candida antarctica lipase B (CAL-B) was initially used to analyze the polyesterification of the 10,16-DHPA (Scheme 1)

Summary

Introduction

The synthesis of aliphatic polyesters continues to be of significant interest in biomedical applications (drug delivery systems, wound closure and healing products, and surgical implant devices) [1,2,3] and some applications that include food containers, soil retention sheeting, agriculture film, waste bags and the use as a packaging material in general [4]. The presence of free functional groups such as hydroxyl and carboxylate in polyesters can efficiently increase their hydrophilicity and degradability, as well as modulate their mechanical, thermal, chemical, and biologic properties [5,6,8]. These functional groups could allow conjugation of a variety of bioactive molecules to obtain novel biomaterials with diverse applications. Poly(malic acid) and polyesters containing L-malic acid units are attractive because of their remarkable advantages in temporary therapeutic applications [9]

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