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

被引:12
作者
Beatriz Gomez-Patino, M. [1 ]
Cassani, Julia [2 ]
Eugenia Jaramillo-Flores, Maria [1 ]
Gerardo Zepeda-Vallejo, L. [1 ]
Sandoval, Georgina [3 ]
Jimenez-Estrada, Manuel [4 ]
Arrieta-Baez, Daniel [5 ]
机构
[1] Inst Politecn Nacl ENCB, Mexico City 11340, DF, Mexico
[2] Univ Autonoma Metropolitana, Unidad Xochimilco, Dept Sistemas Biol, Mexico City 04960, DF, Mexico
[3] CIATEJ, Guadalajara 42270, Jalisco, Mexico
[4] Univ Nacl Autonoma Mexico, Inst Quim, Dept Prod Nat, Mexico City 04510, DF, Mexico
[5] Inst Politecn Nacl CNMN, Unidad Profes Adolfo Lopez Mateos, Mexico City 07738, DF, Mexico
关键词
lipases; oligomerization; natural monomer; tomato cuticle; FRUIT CUTICLE POLYESTERS; ALIPHATIC POLYESTERS; DRUG-DELIVERY; POLYMERIZATION; SUBERIN; COPOLYESTERS; D; L-LACTIDE; COPOLYMER; MONOMER; SYSTEMS;
D O I
10.3390/molecules18089317
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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 degrees 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.
引用
收藏
页码:9317 / 9333
页数:17
相关论文
共 39 条
[32]   Polymeric systems for controlled drug release [J].
Uhrich, KE ;
Cannizzaro, SM ;
Langer, RS ;
Shakesheff, KM .
CHEMICAL REVIEWS, 1999, 99 (11) :3181-3198
[33]  
Uyama H, 2001, MACROMOL BIOSCI, V1, P40, DOI 10.1002/1616-5195(200101)1:1<40::AID-MABI40>3.3.CO
[34]  
2-K
[35]   Biopolymers: overview of several properties and consequences on their applications [J].
Van de Velde, K ;
Kiekens, P .
POLYMER TESTING, 2002, 21 (04) :433-442
[36]  
Wise D.L., 1979, LACTIC GLYCOLIC ACID, P237
[37]   INVIVO BIOCOMPATIBILITY STUDIES OF MEDISORB(R) 65/35 D,L-LACTIDE GLYCOLIDE COPOLYMER MICROSPHERES [J].
YAMAGUCHI, K ;
ANDERSON, JM .
JOURNAL OF CONTROLLED RELEASE, 1993, 24 (1-3) :81-93
[38]   Synthesis and characterization of biodegradable low molecular weight aliphatic polyesters and their use in protein-delivery systems [J].
Zhou, SB ;
Deng, XM ;
Li, XH ;
Jia, WX ;
Liu, L .
JOURNAL OF APPLIED POLYMER SCIENCE, 2004, 91 (03) :1848-1856
[39]  
Zinck P., 2011, SYNTHETIC STRATEGIES