- Highly efficient solvent-free synthesis of 1,3-diacylglycerols by lipase immobilised on nano-sized magnetite particles
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Recently, 1,3-DAGs (1,3-diacylglycerols) have attracted considerable attention as healthy components of food, oil and pharmaceutical intermediates. Generally, 1,3-DAG is prepared by lipase-mediated catalysis in a solvent free system. However, the system's high reaction temperature (required to reach the reactants' melting point), high substrate concentration and high viscosity severely reduce the lipase's activity, selectivity and recycling efficiency. In this report, MjL (Mucor javanicus lipase) was found to have the best performance in the solvent-free synthesis of 1,3-DAGs of several common commercial lipases. By covalent binding to amino-group-activated NSM (nano-sized magnetite) particles and cross-linking to form an enzyme aggregate coat, MjL's specific activity increased 10-fold, and was able to be reused for 10 cycles with 90% residual activity at 55 °C. 1,3-DAGs of lauric, myristic, palmitic, stearic, oleic and linoleic acid were prepared using the resulting immobilised enzyme, all with yields greater than 90%, and the reaction time was also greatly reduced.
- Meng, Xiao,Xu, Gang,Zhou, Qin-Li,Wu, Jian-Ping,Yang, Li-Rong
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p. 319 - 324
(2013/10/08)
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- Use of glycerol carbonate in an efficient, one-pot and solvent free synthesis of 1,3-sn-diglycerides
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An efficient solvent-free synthesis of a variety of highly pure 1,3-sn-diglycerides (1,3-sn-diacylglycerols) in a two-step one pot process is described. Heating glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one) with fatty acid anhydrides 2a-d affords 1:1 mixtures of glycerol carbonate fatty esters 3a-3d and the corresponding fatty acids. Further heating the reaction mixtures in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 195-200 °C yields highly pure 1,3-sn-diglycerides 4a-4d.
- Kargar, Mojgan,Hekmatshoar, Rahim,Ghandi, Mehdi,Mostashari, Abdoljalil
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p. 259 - 264
(2013/07/27)
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- Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite
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Glycerol-fatty acid esterification has been conducted with lipase from Penicillium camembertii lipase immobilized on epoxy SiO2-PVA in solvent-free media, with the major product being 1-monoglyceride, a useful food emulsifier. For a given set of initial conditions, the influence of reaction was measured in terms of product formation and selectivity using different fatty acids as acyl donors. Results were found to be relatively dependent of the chain length of the fatty acids, showing high specificity for both myristic and palmytic acids attaining final mixture that fulfills the requirements established by the World Health Organization to be used as food emulsifiers.
- Freitas, Larissa,Paula, Ariela V.,dos Santos, Julio C.,Zanin, Gisella M.,de Castro, Heizir F.
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experimental part
p. 87 - 90
(2010/10/19)
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- PROPOFOL PHOSPHONYL DERIVATIVES, SYNTHESIS, AND USE IN LONG ACTING FORMULATIONS
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This invention relates to compounds represented by the structural formula (I), and the salts and stereoisomers thereof, wherein: - L is a linker selected from the group consisting of -(CH2)P-O-, a single bond, formula (IA), -(CH2)1-8-O-X(O)-, and - p is an integer from 1 to 8, - each R3 and each R4 is independently selected from the group consisting of C1-20alkyl, C3-12alkyl, C3-12cycloalkyl-C1-4alkyl, saturated heterocyclyl and saturated heterocyclyl-C1-4alkyl, and - X and Y are each independently C or S(O), - Z is selected from the group consisting of O, S(O) and NR5, - W is selected from the group consisting of halogen, OH, S(O)H and O-M+ wherein M+ is a monovalent cation; and - R5 is selected from the group consisting of hydrogen and C1-10 alkyl. These compounds are useful pharmaceutical agents with improved oral bioavailability.
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Page/Page column 25
(2010/11/03)
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- Therapeutic use of acyl glycerols and the nitrogen- and sulphur- containing analogues thereof
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The invention relates to the use of acyl glycerols and the nitrogen- and sulfur-containing analogues thereof in the therapeutic field, particularly in human health. The inventive compounds have advantageous pharmacological properties and are particularly of use for the prevention or treatment of neurodegenerative diseases.
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Page/Page column 30
(2008/06/13)
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- Therapeutic use of of acyglycerols and the nitrogen-and sulphur-containing analogues thereof
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The invention relates to the use of acylglycerols and the nitrogen- and sulfur-containing analogues thereof in therapy, particularly for the treatment of cerebral ischemia. The invention further relates to methods for preparing said derivatives, novel compounds, in particular acylglycerols, the nitrogen- and sulfur-containing analogues thereof and methods for preparing same.
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Page/Page column 14
(2010/11/24)
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- Design of well balanced hydrophilic-lipophilic catalytic surfaces for the direct and selective monoesterification of various polyols
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The transesterification process is a well known reaction of organic chemistry. However, the monoesterification of unprotected polyols such as glycerol or sucrose is much more complex and the design of selective catalysts is becoming a huge challenge in order to avoid many protection and deprotection steps, harmful for the cost and the environmental impact of the resulting process. In this study, we showed that the control of the hydrophilic-lipophilic balance of heterogeneous catalysts is a crucial key in order to tune both the catalyst activity and the monoester selectivity. Indeed, whereas homogeneous guanidine led to low selectivity toward monoesters, its anchorage on a hydrophilic solid support such as silica allowed us to prepare two basic hybrid organic-inorganic materials able to selectively afford monoesters in high yield and in an environmentally-friendly process, at low temperature and starting from an equimolecular mixture of unprotected polyols and various fatty methyl esters. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
- Kharchafi, Ghizlane,Jerome, Francois,Adam, Isabelle,Pouilloux, Yannick,Barrault, Joel
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p. 928 - 934
(2007/10/03)
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- Fatty acid compounds, preparation and uses thereof
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The invention concerns novel molecules, their preparation and their uses, in particular in the field of human and veterinary medicine and cosmetics. The inventive compounds are partly fatty acid derivatives and exhibit advantageous pharmacological and cosmetic properties. The invention also concerns various uses of said compounds, the pharmaceutical compositions containing them and methods for preparing them. The inventive compounds are useful in particular for preventing and/or treating dyslipidemiae, cardiovascular diseases, syndrome X, restenosis, diabetes, obesity, hypertension, certain cancers, dermatological diseases and in cosmetics, for fighting against skin aging and its effects notably against wrinkles and the like
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- Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation
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A highly efficient two-step chemoenzymatic synthesis of structured triacylglycerols comprising a pure n-3 polyunsaturated fatty acid at the mid-position and a pure saturated fatty acid located at the end-positions is described. In the first step an immobilized Candida antarctica lipase was observed to display an excellent regioselectivity toward the end-positions of glycerol at 0-4°C using vinyl esters as acylating agents. The n-3 fatty acids were introduced into the remaining mid-position highly efficient and in excellent yields using EDCI coupling agent.
- Halldorsson, Arnar,Magnusson, Carlos D.,Haraldsson, Gudmundur G.
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p. 9101 - 9109
(2007/10/03)
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- Acid-catalyzed intra- and intermolecular acyl exchange in mono- and diglycerides
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Acid-catalyzed transformation of 1-monolauroylglycerine (1-MLG) was investigated. It has been demonstrated that 1-MLG disproportionates readily and quickly into a mixture of 1,2- and 1,3-diacylglycerines and glycerine. The transformation of 1,3-diglycerides into 1,2-diglycerides was studied.
- Isai,Usol'tsev,Stiba
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p. 325 - 329
(2007/10/03)
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- Synthesis of 2-Modified 1,3-Diacylglycerols
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1,3-Diacylglycerols modified in 2-position were synthesized by combining enzymatic and chemical methods.The syntheses started from the regioisomerically pure 1,3-dilauroylglycerol or 1,3-dimyristoylglycerol obtained from glycerol and vinyl esters of carboxylic acids by means of lipase from Mucor mihei.The 2-hydroxyl group in the glycerol derivatives was subsequently substituted by phosphate as well as its disodium salt, by sulfate, phosphocholine, the benzyloxy, the succinimidyl or the amino group.
- Haftendorn, Regine,Ulbrich-Hofmann, Renate
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p. 1177 - 1186
(2007/10/02)
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- The Synthesis of Some Esters of Glycerol with Special Attention to the Problem of Acyl Migration
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Various triglycerides have been prepared by the acylation of either cis-1,3-O-benzylideneglycerol or 2,3-O-isopropylideneglycerol, followed by removal of the protecting group and acylation of the resultant diol.Alternatively, acylation of dihydroxyacetone, reduction of the intermediate ketone with sodium cyanoborohydride (pH 4) and acylation of the resultant alcohol also provide triglycerides in good yields.In some of these esters of glycerol, 13C n.m.r. spectroscopy (125.7 MHz) was used to monitor potential acyl migration.Finally, 2-halopyridinium salts were investigated as an alternative to the normal dicyclohexylcarbodiimide/dimethylaminopyridine couple for glycerol esterification.
- Cockman, Samantha J.,Joll, Cynthia A.,Mortimer, Bok-Cheng,Redgrave, Trevor G.,Stick, Robert V.
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p. 2093 - 2097
(2007/10/02)
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- The effect of coenzyme Q10 on the action of phospholipase.
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Using dimyristoyl L-alpha-phosphatidylcholine as a substrate, the effect of coenzyme Q10 on phospholipid digestion by phospholipase A2 and phospholipase C was investigated. Free myristic acids released by phospholipase A2, and myristic acids of dimyristoyl glyceride released by phospholipase C were methylated and determined quantitatively by gas-chromatography. Phospholipase A2 or phospholipase C released myristic acids dose-dependently from the substrate. Coenzyme Q10 prevented dose-dependently the hydrolysis of the substrate caused by phospholipase. These results suggest that pharmacological action of coenzyme Q10 could be attributed to its protection of membrane phospholipids against the attack of phospholipases.
- Sugiyama,Hattori,Nagai,Takamura,Ozawa
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