- Synthesis of 1,3-olein-2-palmitin (OPO)
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The present invention concerns a highly selective process for the preparation of an ingredient comprising 1,3-Olein-2-palmitin (OPO), a triglyceride present in human breast milk. The present invention also relates to 1,3-Olein-2-palmitin (OPO) ingredient
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Page/Page column 11
(2022/03/07)
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- Regioisomeric characterization of triacylglycerols using silver-ion HPLC/MS and randomization synthesis of standards
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Silver-ion normal-phase high-performance liquid chromatography (HPLC) provides a superior separation selectivity for lipids differing in the number and position of double bonds in fatty acid chains including the resolution of triacylglycerol (TG) regioiso
- Lisa, Miroslav,Velinska, Hana,Holcapek, Michal
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experimental part
p. 3903 - 3910
(2010/03/23)
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- Characterization of lipases and esterases from metagenomes for lipid modification
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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.
- Bertram, Mark,Hildebrandt, Petra,Weiner, David P.,Patel, Jesal S.,Bartnek, Flash,Hitchman, Timothy S.,Bornscheuer, Uwe T.
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- Atmospheric pressure covalent adduct chemical ionization tandem mass spectrometry for double bond localization in monoene- and diene-containing triacylglycerols
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We report a method to elucidate the structure of triacylglycerols (TAGs) containing monoene or diene fatty acyl groups by atmospheric pressure covalent adduct chemical ionization (APCACI) tandem mass spectrometry using acetonitrile as an adduct formation reagent. TAGs were synthesized with the structures ABB and BAB, where A is palmitate (C16:0) and B is an isomeric C18 monoene unsaturated at position 9, 11, or 13 or an isomeric diene unsaturated at positions 9 and 11, 10 and 12, or 9 and 12. In addition to the species at m/z 54 observed in previous CI studies of fatty acid methyl esters, we also found that ions at m/z 42, 81, and 95 undergo covalent reaction with TAGs containing double bonds to yield ions at m/z 40, 54, 81, and 95 units greater than that of the parent TAG: [M + 40]+, [M + 54]+, [M + 81] +, and [M + 95]+ ions. When collisionally dissociated, these ions fragment to produce two or three diagnostic ions that locate the double bonds in the TAG. In addition, ions [RCH=C=O + 40]+ and [RCH=C=O + 54]+ formed from collisional dissociation are of strong abundance in MS/ MS spectra, and collisional activation of these ions produces two intense confirmatory diagnostic ions in the MS3 spectra. Fragment ions reflecting neutral loss of an sn-1-acyl group from [M + 40]+ and [M + 54]+ are more abundant than those reflecting neutral loss of an sn-2-acyl group, analogous to previous reports for protonated TAGs. The position of each acyl group on the glycerol backbone is thus determined by the relative abundances of these ions. Under the conditions in our instrument, the [M + 40]+ adduct is at the highest signal and also yields all information about the double bond position and TAG stereochemistry. With the exception of geometries about the double bonds, racemic TAG isomers containing two monoenes or dienes and a saturate can be fully characterized by APCACI-MS/MS/MS.
- Xu, Yichuan,Brenna, J. Thomas
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p. 2525 - 2536
(2008/01/04)
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- Synthesis of the structured lipid 1,3-dioleoyl-2-palmitoylglycerol from palm oil
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Human milk fat contains 20-25% palmitic acid (16:0) and 30-35% oleic acid (18:1). More than 60% of the palmitic acid occurs at the sn-2 position of the glycerol backbone. Palm oil is a rich source of both palmitic and oleic acids. The structured lipid 1,3-dioleoyl-2-palmitoylglycerol (OPO) is an important ingredient in infant formula. OPO was synthesized from palm oil by a three-step method. In the first step, low-temperature fractionation was applied to palm oil FA, yielding a palmitic acid-rich fraction (87.8%) and an oleic acid-rich fraction (96%). The palmitic acid content was further increased to 98.3% by transforming palmitic acid into ethyl palmitate. In the second step, esterificalion of ethyl palmitate and glycerol catalyzed by lipase Novozym 435 under vacuum (40 mm Hg) was employed for the synthesis of tripalmitin. Finally, OPO was obtained by the reaction of tripalmitin with oleic acid catalyzed by Lipase IM 60. In this final step, the TAG content in the product acylglycerol mixture was 97%, and 66.1 % oleic acid was incorporated into TAG. Analysis of the FA composition at the sn-2 position of TAG showed 90.7 mol% of palmitic acid and 9.3 mol% of oleic acid. OPO content in the product TAG was ca. 74 mol%. Thus, an efficient method was developed for the synthesis of OPO from palm oil.
- Chen, Ming-Lung,Vali, Shaik Ramjan,Lin, Jih-Yao,Ju, Yi-Hsu
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p. 525 - 532
(2007/10/03)
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- Host-recognizing kairomones for parasitic wasp, Anisopteromalus calandrae, from larvae of azuki bean weevil, Callosobruchus chinensis.
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Host-recognizing kairomones for the stinging behavior of the parasitic wasp, Anisopteromalus calandrae, were identified on host azuki bean weevil larvae, Callosobruchus chinensis (L.). The kairomones were extracted with acetone from Chinese green beans, from which emerged wasps and host weevils had been removed. The kairomones are a mixture of triacylglycerols and fatty acids, each of which is separately active, and with no observable synergistic effect between them. These compounds are known to be constituents of an oviposition-marking pheromone of host azuki bean weevils. However, they differ from the previously reported saturated hydrocarbons and diacylglycerols of the kairomone that another parasitic wasp, Dinarmus basalis, uses for the host recognition of C. chinensis. Thus, A. calandrae and D. basalis selectively utilize different constituents of the oviposition-marking pheromone of C. chinensis as host-recognizing kairomones.
- Onodera, Junko,Matsuyama, Shigeru,Suzuki, Takahisa,Fujii, Koichi
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p. 1209 - 1220
(2007/10/03)
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- Optimization of the reaction conditions in the lipase-catalyzed synthesis of structured triglycerides
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Structured triglycerides of the ABA-type, containing one type of fatty acid (A) in the sn-1 and sn-3 positions and a second type of fatty acid (B) in the sn-2 position of the glycerol, were synthesized using lipases. The highest yields and purities were achieved in a two-step process, where a triglyceride of the B-type was subjected to an alcoholysis reaction in an organic solvent catalyzed by sn-1,3-regiospecific lipases yielding the corresponding 2-monoglyceride (2-MG). Using this strategy, e.g., 2-monopalmitin (2-MP) was obtained in up to 88% yield at >95% purity by crystallization. Esterification of 2-MP with oleic acid resulted in the formation of 1,3-oleyl-2-palmitoyl-glycerol in up to 72% yield containing 94% palmitic acid in the sn-2 position. The best lipases were from Rhizomucor miehei, Rhizopus delemar, and Rhizopus javanicus. Water activity, solvent, and carrier for lipase immobilization strongly influenced the yield and purity of the products in both steps. Furthermore, 2-MG from fish oil were produced by alcoholysis in up to 84% yield at >95% purity.
- Schmid,Bornscheuer,Soumanou,McNeill,Schmid
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p. 1527 - 1531
(2007/10/03)
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- Stereospecific synthesis of selected triglycerides: comments on acyl migration and analysis of configuration
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Symmetrical and stereospecifically defined triglycerides have been prepared from racemic and (R)- and (S)-glycidol, respectively.The synthetic sequence allows the incorporation of sensitive fatty acids such as linolenic acid.Justification for retention of
- Sonnet, Philip E.,Dudley, Robert L.
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p. 185 - 191
(2007/10/02)
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- Synthesis of Triglycerides from 1,3-Dibromopropan-2-ol
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1,3-Dibromopropan-2-ol (I) was converted into an acyl derivative (VI) by reaction with an appropriate acyl chloride in the presence of pyridine.The acyl derivative (VI) was subjected to nucleophilic substitution with 3 mol. equiv. tris(decyl)methylammonium carboxylate in refluxing hexane.This led to symmetrical diacid triglycerides in 90-94percent yield.Substitution with an equimolar amount of the carboxylate afforded, predominantly, the 1,2-bisacyloxy-3-bromopropane (VII) which could be easily isolated and further substituted to give unsymmetrical diacid- and triacid-triglycerides in ca. 96percent yield.Lipolysis showed the synthetic triglycerides to be ca. 99percent pure.
- Bhati, Asharam,Hamilton, Richard J.,Steven, David A.,Aneja, Rajender,Padley, Frederick B.
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p. 1553 - 1558
(2007/10/02)
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