Activation of n-3 polyunsaturated fatty acids as oxime esters: A novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase

Chemistry and Physics of Lipids

Volumn 165, Issue 7, 2012, Pages 712-720

  Magnusson, Carlos D ^a   Haraldsson, Gudmundur G ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

Author keywords

1 O Alkylglycerols; Candida antarctica lipase; Diacylglycerols (DAG); EPA and DHA; Monoacylglyceryl ethers (MAGE); Oxime esters of PUFA

Indexed keywords

DIACYLGLYCEROL; DOCOSAHEXAENOIC ACID; GLYCEROL; ICOSAPENTAENOIC ACID; LIPASE B;

ACYLATION; ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL STRUCTURE; DEPROTECTION REACTION; ENANTIOMER; ISOMERISM; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TRANSESTERIFICATION;

ACYLATION; DIGLYCERIDES; ENZYMES, IMMOBILIZED; ESTERS; ETHERS; FATTY ACIDS, OMEGA-3; FUNGAL PROTEINS; LIPASE; MOLECULAR STRUCTURE; MONOGLYCERIDES; OXIMES; STEREOISOMERISM;

CANDIDA ANTARCTICA;

EID: 84865957884     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2012.07.005     Document Type: Article

References (60)

1. R. Acevedo, D. Gil, J. del Campo, G. Bracho, Y. Valdes, and O. Perez The adjuvant potential of synthetic alkylglycerols Vaccine 24 Suppl. 2 2006 32 33
2. B.M. Anderson, and D.W. Ma Are all n-3 polyunsaturated fatty acids created equal? Lipids in Health and Disease 8 2009 33
3. G. Aranda, and L. Blanco Regioselective enzymatic synthesis of glycerol derivatives Synthetic Communications 22 1992 135 144
4. S. Bloomer, P. Adlercreutz, and B. Mattiasson Triglyceride interesterification by lipases. 2. Reaction parameters for the reduction of trisaturated impurities and diglycerides in batch reactions Biocatalysis 5 1991 145 162
5. D.C. Chan, M.N. Nguyen, G.F. Watts, E.M.M. Ooi, and P.H.R. Barrett Effects of atorvastatin and n-3 fatty acid supplementation on VLDL apolipoprotein C-III kinetics in men with abdominal obesity American Journal of Clinical Nutrition 91 2010 900 906
6. W.N. Charman, and C.J.H. Porter Lipophilic prodrugs designed for intestinal lymphatic transport Advanced Drug Delivery Reviews 19 1996 149 169
7. C. Cheminade, V. Gautier, A. Hichami, P. Allaume, D. Le Lannou, and A.B. Legrand 1-O-Alkylglycerols improve boar sperm motility and fertility Biology of Reproduction 66 2002 421 428
8. R. Chenevert, N. Pelchat, and F. Jacques Stereoselective enzymatic acylations (transesterifications) Current Organic Chemistry 10 2006 1067 1094
9. M.S. Christensen, and C.E. Hoy Effects of dietary triacylglycerol structure on triacylglycerols of resultant chylomicrons from fish oil- and seal oil-fed rats Lipids 31 1996 341 344
10. W.W. Christie Lipid Analysis 2nd ed. 1982 Pergamon Press New York
11. R. Colomer, J.M. Moreno-Nogueira, P.P. Garcia-Luna, P. Garcia-Peris, A. Garcia-de-Lorenzo, A. Zarazaga, L. Quecedo, J. del Llano, L. Usan, and C. Casimiro N-3 fatty acids, cancer and cachexia: a systematic review of the literature British Journal of Nutrition 97 2007 823 831
12. D.L. Compton, K.E. Vermillion, and J.A. Laszlo Acyl migration kinetics of 2-monoacylglycerols from soybean oil via H-1 NMR Journal of the American Oil Chemists Society 84 2007 343 348
13. M. Degueil-Castaing, B. De Jeso, S. Drouillard, and B. Maillard Enzymatic reactions in organic synthesis: 2-ester interchange of vinyl esters Tetrahedron Letters 28 1987 953 954
14. A.L. Deniau, P. Mosset, F. Pedrono, R. Mitre, D. Le Bot, and A.B. Legrand Multiple beneficial health effects of natural alkylglycerols from shark liver oil Marine Drugs 8 2010 2175 2184
15. J.S. Dordick Enzymatic catalysis in monophasic organic-solvents Enzyme and Microbial Technology 11 1989 194 211
16. K. Faber 3.1.1 Ester synthesis K. Faber, Biotransformations in Organic Chemistry 2004 Springer-Verlag Berlin 344 349
17. A.M. Fureby, C. Virto, P. Adlercreutz, and B. Mattiasson Acyl group migrations in 2-monoolein Biocatalysis and Biotransformation 14 1996 89 111
18. A. Ghogare, and G.S. Kumar Oxime esters as novel irreversible acyl transfer agents for lipase catalysis in organic media Journal of the Chemical Society-Chemical Communications 1989 1533 1535
19. D. Gopinath, D. Ravi, B.R. Rao, S.S. Apte, and D. Rambhau 1-O-Alkylglycerol vesicles (Algosomes): their formation and characterization International Journal of Pharmaceutics 246 2002 187 197
20. A. Halldorsson, B. Kristinsson, and G.G. Haraldsson Lipase selectivity toward fatty acids commonly found in fish oil European Journal of Lipid Science and Technology 106 2004 79 87
21. A. Halldorsson, C.D. Magnusson, and G.G. Haraldsson Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation Tetrahedron 59 2003 9101 9109
22. A. Halldorsson, P. Thordarson, B. Kristinsson, C.D. Magnusson, and G.G. Haraldsson Lipase-catalysed kinetic resolution of 1-O-alkylglycerols by sequential transesterification Tetrahedron: Asymmetry 15 2004 2893 2899
23. B. Hallgren Therapeutic effects of ether lipids H.K. Mangold, F. Paltauf, Ether Lipids: Biochemical and Biomedical Aspects 1983 Academic Press New York 261 275
24. J.L. Hammond, D.L. Koontz, H.Z. Bazmi, J.R. Beadle, S.E. Hostetler, G.D. Kini, K.A. Aldern, D.D. Richman, K.Y. Hostetler, and J.W. Mellors Alkylglycerol prodrugs of phosphonoformate are potent in vitro inhibitors of nucleoside-resistant human immunodeficiency virus type 1 and select for resistance mutations that suppress zidovudine resistance Antimicrobial Agents and Chemotherapy 45 2001 1621 1628
25. G.G. Haraldsson Chemoenzymatic synthesis of structured lipids positionally labeled with pure fatty acids C.T. Hou, J.F. Shaw, Biocatalysis and Biotechnology for Functional Foods and Industrial Products 2007 CRC Taylor and Francis Boca Raton 57 77
26. G.G. Haraldsson, and O. Almarsson Studies on the positional specificity of lipase from Mucor miehei during interesterification reactions of cod liver oil with n-3 polyunsaturated fatty acid and ethyl ester concentrates Acta Chemica Scandinavica 45 1991 723 730
27. G.G. Haraldsson, B.O. Gudmundsson, and O. Almarsson The synthesis of homogeneous triglycerides of eicosapentaenoic acid and docosahexaenoic acid by lipase Tetrahedron 51 1995 941 952
28. G.G. Haraldsson, A. Halldorsson, and E. Kulas Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids Journal of the American Oil Chemists Society 77 2000 1139 1145
29. G.G. Haraldsson, and B. Hjaltason PUFA production from marine sources for use in food F.D. Gunstone, Modifying Lipids for Use in Food 2006 Woodhead Publishing Cambridge, UK 336 368
30. G.G. Haraldsson, and A. Thorarensen The generation of glyceryl ether lipids highly enriched with eicosapentaenoic acid and docosahexaenoic acid by lipase Tetrahedron Letters 35 1994 7681 7684
31. W.S. Harris, P.M. Kris-Etherton, and K.A. Harris Intakes of long-chain omega-3 fatty acid associated with reduced risk for death from coronary heart disease in healthy adults Current Atherosclerosis Reports 10 2008 503 509
32. D.J. Holub, and B.J. Holub Omega-3 fatty acids from fish oils and cardiovascular disease Molecular and Cellular Biochemistry 263 2004 217 225
33. S.M. Hoy, and G.M. Keating Omega-3 ethylester concentrate: a review of its use in secondary prevention post-myocardial infarction and the treatment of hypertriglyceridaemia Drugs 69 2009 1077 1105
34. Y. Iwasaki, and T. Yamane Enzymatic synthesis of structured lipids Journal of Molecular Catalysis B: Enzymatic 10 2000 129 140
35. M.J. James, S.M. Proudman, and L.G. Cleland Dietary n-3 fats as adjunctive therapy in a prototypic inflammatory disease: issues and obstacles for use in rheumatoid arthritis Prostaglandins Leukotrienes and Essential Fatty Acids 68 2003 399 405
36. M. Kayama, and M. Mankura Natural oleochemicals in marine fishes Inform 9 1998 794 799
37. D.R. Kodali, A. Tercyak, D.A. Fahey, and D.M. Small Acyl migration in 1,2-dipalmitoyl-sn-glycerol Chemistry and Physics of Lipids 52 1990 163 170
38. A.M.P. Koskinen, and A.M. Klibanov Enzymatic Reactions in Organic Media 1st ed. 1996 Blackie Academic and Professional London
39. D.M. Lambert Rationale and applications of lipids as prodrug carriers European Journal of Pharmaceutical Sciences 11 2000 S15 S27
40. J.A. Laszlo, D.L. Compton, and K.E. Vermillion Acyl migration kinetics of vegetable oil 1,2-diacylglycerols Journal of the American Oil Chemists Society 85 2008 307 312
41. C.D. Magnusson, A.V. Gudmundsdottir, and G.G. Haraldsson Chemoenzymatic synthesis of a focused library of enantiopure structured 1-O-alkyl-2,3-diacyl- sn-glycerol type ether lipids Tetrahedron 67 2011 1821 1836
42. C.D. Magnusson, and G.G. Haraldsson Chemoenzymatic synthesis of symmetrically structured triacylglycerols possessing short-chain fatty acids Tetrahedron 66 2010 2728 2731
43. C.D. Magnusson, and G.G. Haraldsson Ether lipids Chemistry and Physics of Lipids 164 2011 315 340
44. H. Mangold, and F. Paltauf Ether Lipids: Biochemical and Biomedical Aspects 1st ed. 1983 Academic Press New York p. 439
45. F. Moris, and V. Gotor Selective aminoacylation of nucleosides through an enzymatic reaction with oxime aminoacyl esters Tetrahedron 50 1994 6927 6934
46. B.Z. Ngwenya, and D.M. Foster Enhancement of antibody production by lysophosphatidylcholine and alkylglycerol Proceedings of the Society for Experimental Biology and Medicine 196 1991 69 75
47. F. Pedrono, B. Martin, C. Leduc, J. Le Lan, B. Saiag, P. Legrand, J.P. Moulinoux, and A.B. Legrand Natural alkylglycerols restrain growth and metastasis of grafted tumors in mice Nutrition and Cancer 48 2004 64 69
48. M. Peet, and C. Stokes Omega-3 fatty acids in the treatment of psychiatric disorders Drugs 65 2005 1051 1059
49. B.M. Ross, J. Seguin, and L.E. Sieswerda Omega-3 fatty acids as treatments for mental illness: which disorder and which fatty acid? Lipids in Health and Disease 6 2007 21
50. M.M. Salunkhe, and R.V. Nair Mild and efficient enzymatic oximolysis by supported Pseudomonas cepacia lipases Journal of Molecular Catalysis B: Enzymatic 10 2000 535 538
51. I. Savelieva, A. Kourliouros, and J. Camm Primary and secondary prevention of atrial fibrillation with statins and polyunsaturated fatty acids: review of evidence and clinical relevance Naunyn-Schmiedebergs Archives of Pharmacology 381 2010 1 13
52. A.P. Simopoulos Omega-3 fatty acids in inflammation and autoimmune diseases Journal of the American College of Nutrition 21 2002 495 505
53. T. Storz, J. Gu, B. Wilk, and E. Olsen Regioselective lipase-catalyzed acylation of 41-desmethoxy-rapamycin without vinyl esters Tetrahedron Letters 51 2010 5511 5515
54. S.W. Tsai, and C.M. Huang Enantioselective synthesis of (S)-suprofen ester prodrugs by lipase in cyclohexane Enzyme and Microbial Technology 25 1999 682 688
55. H.S. Ved, E. Gustow, V. Mahadevan, and R.A. Pieringer Dodecylglycerol. A new type of antibacterial agent which stimulates autolysin activity in Streptococcus faecium ATCC 9790 Journal of Biological Chemistry 259 1984 8115 8121
56. C. Waldinger, and M. Schneider Enzymatic esterification of glycerol III. Lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols and 1(3)-rac-monoacylglycerols derived from unsaturated fatty acids Journal of the American Oil Chemists Society 73 1996 1513 1519
57. Y.F. Wang, J.J. Lalonde, M. Momongan, D.E. Bergbreiter, and C.H. Wong Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars and organometallics Journal of the American Chemical Society 110 1988 7200 7205
58. K. Weissermel, and H.J. Arpe K. Weissermel, H.J. Arpe, Industrial Organic Chemistry 4th ed. 2003 Wiley-VCH Weinheim 236 237
59. B.M. Wetherbee, and P.D. Nichols Lipid composition of the liver oil of deep-sea sharks from the Chatham Rise, New Zealand Comparative Biochemistry and Physiology B: Comparative Biochemistry 125 2000 511 521
60. N. Yamamoto, and B.Z. Ngwenya Activation of mouse peritoneal macrophages by lysophospholipids and ether derivatives of neutral lipids and phospholipids Cancer Research 47 1987 2008 2013