111-62-6Relevant articles and documents
Characterization of lipases and esterases from metagenomes for lipid modification
Bertram, Mark,Hildebrandt, Petra,Weiner, David P.,Patel, Jesal S.,Bartnek, Flash,Hitchman, Timothy S.,Bornscheuer, Uwe T.
, p. 47 - 53 (2008)
Three hundred and fifty novel lipases and esterases discovered from environmental DNA samples were characterized for their fatty acid profile using GC-analysis. Enzymes were selected for further study based on activity and fatty acid chain length specificity. Additional characterization was based on enzyme activity towards tributyrin and 4-methylumbelliferyl butyrate, and enzyme heat stability. Several lipases were identified, which show high specificity towards short-chain fatty acids similar to pregastric lipases from kid and calf and a lipase from Mucor javanicus. Additionally, the metagenome-derived enzymes were thermostable. Selected metagenomic lipases were immobilized on Celite and used for the synthesis of structured triglycerides.
Purification of 2-monoacylglycerols using liquid CO2 extraction
Compton, David L.,Eller, Fred J.,Laszlo, Joseph A.,Evans, Kervin O.
, p. 1529 - 1536 (2012)
The fatty acid moiety of 2-monoacyl-sn-glycerol (2-MAG) undergoes spontaneous acyl migration to the sn-1(3) position, resulting in a thermodynamic equilibrium of approximately 1:9 of 2-MAG to 1(3)-monoacyl-sn-glycerol (1-MAG). Spontaneous acyl migration is an impediment to synthesizing and isolating specific 2-MAG for use as intermediates in the synthesis of structured triacylglycerols. 2-Monooleoyl-sn-glycerol was synthesized by the enzymatic ethanolysis of triolein and isolated by liquid CO2 extraction. The resultant MAG, diacylglycerol, and fatty acid ethyl esters were quantified by 1H NMR and supercritical fluid chromatography. The low polarity of the CO2 and mild extraction temperature (25 °C) resulted in very low spontaneous acyl migration rates, allowing the MAG to be isolated in 80% yield and in a very high 2-MAG:1-MAG ratios of ≥93 mol%.
About the role of typical spacer/crosslinker on the design of efficient magnetic biocatalysts based on nanosized magnetite
Nicolás, Paula,Lassalle, Verónica L.,Ferreira, María L.
, p. 296 - 304 (2015)
The immobilization of Candida antarctica lipase B (CALB) was carried out using glutaraldehyde (GLUT) and/or 3-aminopropyl-triethoxisilane (APTS). The aim of this work was to elucidate the role of these crosslinkers/functionalizers on the efficiency of the prepared nanosized catalysts in solvent-free oleic acid esterification. A series of biocatalysts were prepared in presence or absence of GLUT and APTS. The impact of the amount of initial CALB was also explored. An experimental design was utilized to study the variables that maximize biocatalyst activity. A strong dependence of enzymatic activity with the nominal amount of GLUT as well as the final protein/CALB loading was found. Nominal quantity of APTS did not affect catalyst's activity when used in combination with GLUT. Additional studies demonstrated that stability during storage was mainly dependent on the enzyme loading. The optimum biocatalyst was reused six cycles without mass loss. Biocatalyst's performance decreased with reuse. Mechanisms justifying these results were proposed. The role of GLUT and APTS on stability during storage and on differences between initial enzymatic activity and the performance in the reaction after two months was discussed. The problem of mixed interaction of CALB (covalent bonding plus simple adsorption) was carefully addressed to explain leaching of the lipase. Leaching and stability on storage should be included in the analysis of modifiers impact when support's modifiers are used. The fresh and stored biocatalyst enzymatic activity has to be addressed looking at the practical aspects of implementation in technological settings.
Conversion of a carboxylesterase into a triacylglycerol lipase by a random mutation
Reyes-Duarte, Dolores,Polaina, Julio,Lopez-Cortes, Nieves,Alcalde, Miguel,Plou, Francisco J.,Elborough, Kieran,Ballesteros, Antonio,Timmis, Kenneth N.,Golyshin, Peter N.,Ferrer, Manuel
, p. 7553 - 7557 (2005)
A true convert: The carboxylesterase enzyme R.34 (see picture) can be converted into a triacylglycerol lipase without modification of the shape, size, or hydrophobicity of the substrate binding site. The substitution of Asn33 by Asp results in a salt bridge between the Asp33 and Arg49, which causes a distortion of the enzyme structure that makes the catalytic site more accessible to larger substrates but also more labile. (Figure Presented).
Cellulose as an efficient matrix for lipase and transaminase immobilization
De Souza, Stefania P.,Junior, Ivaldo I.,Silva, Guilherme M. A.,Miranda, Leandro S. M.,Santiago, Marcelo F.,Leung-Yuk Lam, Frank,Dawood, Ayad,Bornscheuer, Uwe T.,De Souza, Rodrigo O. M. A.
, p. 6665 - 6671 (2016)
Immobilization of enzymes is important to improve their stability and to facilitate their recyclability, aiming to make biocatalytic processes more efficient. One of the important aspects is the utilization of cheap, abundant, and environmentally friendly carriers for enzyme immobilization. Here we report the use of functionalized cellulose for lipase and transaminase immobilization. High immobilization efficiencies (up to 90%) could be achieved for the transaminase from Vibrio fluvialis. For immobilized lipase CAL-B as well as the transaminase, good conversions and recyclability could be demonstrated in kinetic resolutions to afford chiral alcohols or amines. Moreover, such application of the immobilized transaminase enabled very high conversions in a continuous-flow process in the asymmetric synthesis of (S)-phenylethylamine (80% conversion, >99% ee).
Zirconocene-catalysed biodiesel synthesis from vegetable oil with high free fatty acid contents
Deng, Yiqiang,Hu, Xiaojian,Cheng, Lihua,Wang, Hanlu,Duan, Linhai,Qiu, Renhua
, p. 116 - 120 (2018)
A highly efficient transformation of vegetable oils into biodiesel catalysed by air-stable and water-tolerant zirconocene perfluorooctanesulfonate Lewis acid has been developed. By combining the direct esterification of free fatty acids (FFAs) and transesterification of triglycerides (TGs), the simultaneous transformation of the two components to biodiesel is achieved in good yields. Furthermore, this catalyst, when used in the synthesis of biodiesel from commercial oleifera, behaves as a reaction-induced self-separation catalyst. During the course of the reaction, it switches from homogeneous to heterogeneous; upon completion of the reaction, the catalyst precipitates as a white solid, which can be easily recycled.
Synthesis of a Palm-Based Star-Shaped Hydrocarbon via Oleate Metathesis
Choo, Yuen-May,Ooi, Kay-Eng,Ooi, Ing-Hong,Tan, Daniel D. H.
, p. 333 - 336 (1996)
10,11-Dioctyleicosane, a star-shaped hydrocarbon, has been successfully synthesized from 9-octadecene (a product from metathesis of methyl oleate or ethyl oleate) through dimerization followed by hydrogenation.The product was determined by 13C nuclear magnetic resonance spectroscopic and gas chromatography/mass spectrometric techniques.This hydrocarbon likely exhibits lubricating properties that can be used as high-performance functional fluids in automotive lubrication.We also report the presence of a novel product, a trimer that was formed during the synthesis. - Key words: Diethyl 9-octadecenedioate; 10,11-dioctyl eicosane; ethyl and methyl oleates; metathesis; 9-octadecene; palm oil; star-shaped hydrocarbon.
Evaluating the kinetics of the esterification of oleic acid with homo and heterogeneous catalysts using in-line real-time infrared spectroscopy and partial least squares calibration
Kartnaller, Vinicius,Junior, Ivaldo I.,De Souza, Adriana V.A.,Costa, Ingrid C.R.,Rezende, Michelle J.C.,Da Silva, Jo?o F. Cajaiba,De Souza, Rodrigo O.M.A.
, p. 41 - 46 (2016)
Biodiesel is a mixture of fatty acid alkyl esters with properties similar to petroleum-based diesel. Thus, biodiesel can be used as either a substitute for diesel fuel or, more commonly, in a fuel blend. Biodiesel production can be catalyzed with mineral acids or bases or enzymes. The use of real-time techniques for monitoring the reaction and evaluating the efficiency of the catalyst can be of great use for optimizing the reaction and monitoring the process. In the present work, an in-line real-time methodology was used to evaluate and compare the kinetics of a reaction catalyzed with homo (hydrochloric acid) and heterogeneous (the enzymes Novozym 435, Lipozyme RM, and Lipozyme TL) catalysts. The esterification of oleic acid with ethanol was used as the reaction model. The study used attenuated total reflexion/Fourier transform infrared (ATR/FT-IR) and a single partial least squares (PLS) regression model to evaluate the kinetics of the various catalysts, without multiple calibrations, with validation by GC-MS. Novozym 435, which showed complete conversion after 165 min, was the best catalyst for this reaction. Lipozyme RM and Lipozyme TL had inferior conversion after the same amount of time, in agreement with the literature. All enzymatic catalysts showed higher conversion than hydrochloric acid at the same reaction conditions.
Palladium-Catalyzed Directed meta-Selective C?H Allylation of Arenes: Unactivated Internal Olefins as Allyl Surrogates
Achar, Tapas Kumar,Zhang, Xinglong,Mondal, Rahul,Shanavas,Maiti, Siddhartha,Maity, Sabyasachi,Pal, Nityananda,Paton, Robert S.,Maiti, Debabrata
, p. 10353 - 10360 (2019)
Palladium(II)-catalyzed meta-selective C?H allylation of arenes has been developed utilizing synthetically inert unactivated acyclic internal olefins as allylic surrogates. The strong σ-donating and π-accepting ability of pyrimidine-based directing group facilitates the olefin insertion by overcoming inertness of the typical unactivated internal olefins. Exclusive allyl over styrenyl product selectivity as well as E stereoselectivity were achieved with broad substrate scope, wide functional-group tolerance, and good to excellent yields. Late-stage functionalisations of pharmaceuticals were demonstrated. Experimental and computational studies shed light on the mechanism and point to key steric control in the palladacycle, thus determining product selectivities.
Enzyme-Decorated Covalent Organic Frameworks as Nanoporous Platforms for Heterogeneous Biocatalysis
Oliveira, Felipe L.,de Souza, Stefania P.,Bassut, Jonathan,álvarez, Heiddy M.,Garcia-Basabe, Yunier,Alves de Souza, Rodrigo O. M.,Esteves, Pierre M.,Gon?alves, Raoni S. B.
, p. 15863 - 15870 (2019)
Sustainability in chemistry heavily relies on heterogeneous catalysis. Enzymes, the main catalyst for biochemical reactions in nature, are an elegant choice to catalyze reactions due to their high activity and selectivity, although they usually suffer from lack of robustness. To overcome this drawback, enzyme-decorated nanoporous heterogeneous catalysts were developed. Three different approaches for Candida antarctica lipase B (CAL-B) immobilization on a covalent organic framework (PPF-2) were employed: physical adsorption on the surface, covalent attachment of the enzyme in functional groups on the surface and covalent attachment into a linker added post-synthesis. The influence of the immobilization strategy on the enzyme uptake, specific activity, thermal stability, and the possibility of its use through multiple cycles was explored. High specific activities were observed for PPF-2-supported CAL-B in the esterification of oleic acid with ethanol, ranging from 58 to 283 U mg?1, which was 2.6 to 12.7 times greater than the observed for the commercial Novozyme 435.
In situ monitoring of turbid immobilized lipase-catalyzed esterification of oleic acid using fiber-optic Raman spectroscopy
Elfanso, Erick,Garland, Marc,Loh, Kai Chee,Talukder, M.M. Rahman,Widjaja, Effendi
, p. 223 - 226 (2010)
Raman spectroscopy with a fiber-optic probe was used to monitor the immobilized Candida antarctica lipase B (Novozym 435)-catalyzed esterification of oleic acid with ethanol in iso-octane as an organic solvent. The effects of reaction temperature and molar ratio of substrates were studied. An optimal reaction rate was found at 60 °C, beyond which deactivation due to denaturing of the lipase was observed. The variation in molar ratio of substrates suggests that the esterification of oleic acid and ethanol proceeds via a Ping-Pong Bi-Bi mechanism with ethanol exhibiting an inhibitory effect. A good fit was obtained between the experimental results and the best-fit Ping-Pong Bi-Bi mechanism. This current work shows that fiber-optic Raman spectroscopy is indeed a suitable instrument to monitor immobilized lipase-catalyzed reaction in turbid organic systems in situ. Since this approach is reliable, simple to use, allows automatic data acquisition, and accurate, it should be applicable to the detailed kinetic analysis on other immobilized enzymatic reactions as well.
IONIZABLE LIPIDS FOR NUCLEIC ACID DELIVERY
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Paragraph 00330-00332, (2021/01/23)
The present document describes compounds, or pharmaceutically acceptable salt thereof, of a core formula (I) Wherein R1 includes an amino group. These compounds are particularly useful in the formulation and in vivo and ex vivo delivery of nucleic acid and protein therapeutics for preparing and implementing T cell transfection, gene editing, cancer therapies, cancer prophylactics, and in the preparation of vaccines.
NATURAL BIOSURFACTANT OF ESTER AND MANUFACTURING METHOD THEREOF
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Paragraph 0125; 0126; 0129-0132, (2020/12/11)
The present invention relates to an ester natural surfactant and a manufacturing method thereof. The present invention relates to an eco-friendly ester natural surfactant having excellent solubility in water and biodegradability, and a manufacturing method thereof. The present invention relates to an ester natural surfactant, and more particularly, to an ester natural surfactant and a method for preparing the same. (by machine translation)
Method for synthesizing oleic acid low-alcohol ester
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Paragraph 0046-0051, (2019/11/12)
The invention relates to the technical field of organic synthesis and particularly discloses a method for synthesizing oleic acid low-alcohol ester. According to the method, specific Bronsted-Lewis acidic ionic liquid is taken as a catalyst, catalytic oleic acid and low alcohols are subjected to an esterification reaction, and thus corresponding oleate is obtained. The selected ionic liquid has high selectivity to the esterification reaction of the oleic acid and the low alcohols, the use amount is small, and the catalytic efficiency is high.
