Enzymatic modification of phospholipids and related polar lipids

Phospholipid Technology and Applications

Volumn , Issue , 2008, Pages 41-82

  Xu, Xuebing ^a,b   Vikbjerg, Anders Falk ^a   Guo, Zheng ^a   Zhang, Long ^a   Acharya, Ashish kumar ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMATIC MODIFICATION; POLAR LIPIDS;

PHOSPHOLIPIDS;

EID: 84886081902     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1533/9780857097880.41     Document Type: Chapter

References (145)

1. Adlercreutz P., Virto C., Persson M., Vaz S., Adlercreutz D., Svensson I., Wehtje E. Enzymatic conversion of polar lipids. Principles, problems and solutions. Journal of Molecular Catalysis B: Enzymatic 2001, 11:173-178.
2. Adlercreutz D., Budde H., Wehtje E. Synthesis of phosphatidylcholine with defined fatty acid in the sn-1 position by lipase-catalysed esterification and transesterification reaction. Biotechnology and Bioengineering 2002, 78:403-411.
3. Adlercreutz P., Lyberg A.-M., Adlercreutz D. Enzymatic fatty acid exchange in glycerophospholipids. European Journal of Lipid Science and Technology 2003, 105:638-645.
4. Aurich I., Durrschmidt P., Hirche F., Ulbrich-Hofmann R. Transesterification of alkylphosphate esters by phospholipase D. Biotechnology Letters 1997, 19:875-879.
5. Aurich I., Dürrschmidt P., Hirche F., Ulbrich-Hofmann R. Production of octadecylphospho-l-serine by phospholipase D. Biotechnology Letters 2002, 24:585-590.
6. Benning C., Ohta H. Three enzyme systems for galactoglycerolipid biosynthesis are co-ordinately regulated in plants. Journal of Biochemistry 2005, 280:2397-2400.
7. Bjorkling F., Godtfredsen S.E. New enzyme catalysed synthesis of monoacyl galactoglycerides. Tetrahedron 1988, 44:2957-2962.
8. Bueschelberger H.-G. Lecithins. Emulsifiers in Food Technology 2004, 1-39. Blackwell Publishing Ltd, Oxford. R.J. Whitehurst (Ed.).
9. Bugaut M., Kuksis A., Myher J.J. Loss of sterospecificity of phospholipase C and D upon introduction of a 2-alkyl group into rac-1,2-diacylglycero-3-phosphocholine. Biochimica et Biophysica Acta 1985, 835:304-314.
10. Buikstra F.P.M., van der Kruis A.J.M.M., van der Heiden P.H.N. Heat stable oil-inwater emulsion stabilized by hydrolysates 1997, USP 5650190.
11. Carlsson A., Herslof B. Lipophilic carrier preparation 1998, USP 5716639.
12. Carlsson A., Delogu M., Herslof B. Oil-in water emulsions 1997, USP 5688528.
13. Carlsson A., Herslof B., Petrovic-Kallholm S. Bilayers preparations 2000, USP 6022561.
14. Chmiel O., Melachouris N., Tritler H. Process for the interesterification of phospholipids 1999, USP 5989599.
15. Chung G.H., Yang Y.L. Method for preparing lysophosphatidylethaolamine 2004, USP 6773902.
16. Clausen K. Enzymatic oil-degumming by novel microbial phospholipase. European Journal of Lipid Science and Technology 2001, 103:333-340.
17. Coderch L., Lopez O., de la Maza A., Parra J.L. Ceramides and skin function. American Journal of Clinical Research 2003, 4:107-129.
18. Colarow L., Masson G., Truek H.U. Heat stable oil and water emulsion and preparation thereof 1994, USP 5314706.
19. Colombo D., Ronchetti F., Scala A., Taino I.M., Albini F.M., Toma L. Optically pure 1-O-beta-d-glucosyl-sn-glycerols and 3-O-beta-d-glucosyl-sn-glycerols and galactosayl-sn-glycerols through lipase-catalyzed transformations. Tetrahedron Letters 1995, 36:4865-4868.
20. Colombo D., Scala A., Taino I.M., Toma L., Ronchetti F. 1-O-, 2-O- and 3-O-β-d-glycosyl-sn-glycerols: Structure-anti-tumor promoting activity relationship. Bioorganic & Medicinal Chemistry Letters 1996, 6:1187-1190.
21. Colombo D., Ronchetti F., Scala A., Toma L. Bioactive glycoglycerolipid analogues: an expeditious enzymatic approach to mono- and diesters of 2-O-β-Dgalactosylglycerol. Tetrahedron: Asymmetry 1998, 9:2113-2119.
22. Colombo D., Scala A., Taino I.M., Toma L., Ronchetti F., Tokuda H., Nishino H., Nagastu A., Sakakibara J. Inhibitory effects of fatty acid monoesters of 2-O-β-Dglucosylglycerol on Epstein-Barr virus activation. Cancer Letters 1998, 123:83-86.
23. Colombo D., Compostella F., Ronchetti F., Scala A., Tokuda H., Nishino H. Diesters of glycosylglycerols active in cancer chemoprevention. European Journal of Medical Chemistry 2001, 36:691-695.
24. Colombo D., Compostella F., Ronchetti F., Reza-Elahi S., Scala A., Toma L., Aoi W., Kuchide M., Takayasu J., Tokuda H., Nishino H. Inhibitory effect of stabilized analogues of glycoglycerolipids on Epstein-Barr virus activation and mouse skin tumor promotion. Cancer Letters 2002, 186:37-41.
25. Colombo D., Franchini L., Toma L., Ronchetti F., Tanaka R., Takayasu J., Nishino H., Tokuda H. Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity. European Journal of Medical Chemistry 2006, 41:1456-1463.
26. D'Arrigo P., Servi S. Using phospholipases for phospholipid modification. Trends in Biotechnology 1997, 15:90-96.
27. D'Arrigo P., de Ferra L., Piergianni V., Ricci A., Scarcelli D. Phospholipase D from Streptomyces catalyses the transfer of secondary alcohols. Journal of Chemical Society: Chemical Communications 1994, 14:1709-1710.
28. de Roode B.M., Peters S.W.P.G., Fransen M.C.R., van der Padt A., Boom R.M. Optimisation and downstream processing of the almond-β-glucosidase mediated glucosylation of glycerol. Biotechnology and Bioengineering 2001, 72:568-572.
29. de Roode B.M., Fransen M.C.R., van der Padt A., Boom R.M. Perspectives for the industrial enzymatic production of glycosides. Biotechnology Progress 2003, 19:1391-1402.
30. Dittrich N., Ulbrich-Hofmann R. Transphosphatidylation by immobilized phospholipase D in aqueous media. Biotechnology and Applied Biochemistry 2001, 34:189-194.
31. Dittrich N., Haftendorn R., Ulbrich-Hofmann R. Hexadecylphosphocholine and 2-modified 1,3-diacylglycerols as effectors of phospholipiase D. Biochimica et Biophysica Acta 1998, 1391:265-272.
32. Doig S.D., Diks R.M.M. Toolbox for exchanging constituent fatty acids in lecithin. European Journal of Lipid Science and Technology 2003, 105:359-367.
33. Doig S.D., Diks R.M.M. Toolbox for modification of the lecithin headgroup. European Journal of Lipid Science and Technology 2003, 105:368-376.
34. Dubber M., Patel A., Sadalapure K., Aumuller I., Lindhorst T.K. Synthesis of functionalised amphiphilic glycoconjugates and glycoclusters. European Journal of Organic Chemistry 2006, 5357-5366.
35. Egger D., Wehtje E., Adlercreutz P. Characterization and optimization of Phospholipase A2 catalyzed synthesis of phosphatidylcholine. Biochimica et Biophysica Acta 1997, 1343:76-84.
36. Eibl H., Unger C. Phospholipids-selective drugs in cancer-therapy. Proceedings of Social and Experimental Biology and Medicine 1998, 29:358. 358.
37. Elimelech R. Process for large-scale preparation of sphingosines and ceramides 2002, USP 6469148 B1.
38. Fogarty W.M., Benson C.P. Measurment of glucoside transfer to glycerol by Aspergilus niger transglucosidase. Biotechnology Letters 1982, 4:61-64.
39. Frohman M.A., Morris A.J. Phospholipase D structure and regulation. Chemistry and Physics of Lipids 1999, 98:127-140.
40. Fujima T., Frusawa H., Minamikawa H., Ito K., Shimizu T. Elastic precursor of the transformation from glycolipids nanotube to vesicle. Journal of Physics: Condensed Matter 2006, 18:3089-3096.
41. Garcia-Junceda E., Garcia-Garcia J.F., Bastida A., Fernandez-Meyoralas A. Enzymes in the synthesis of bioactive compounds: the prodigious decades. Bioorganic and Medicinal Chemistry 2004, 12:1817-1834.
42. Geho W.B. Lipid membrane structure for drug delivery and composition containing a lipid membrane drug system 1980, EP 0009842.
43. Gill I., Valivety R. Enzymatic glycosylation in plasticized glass phases: A novel and efficient route to O-glycosides. Angewandte Chemie International Edition 2000, 39:3804-3808.
44. Guo Z., Vikbjerg A.F., Xu X. Enzymatic modification of phospholipids for functional applications and human nutrition. Biotechnology Advances 2005, 23:203-259.
45. Haraldsson G.G., Thorarensen A. Preparation of phospholipids highly enriched with n-3 polyunsaturated fatty acids by lipase. Journal of the American Oil Chemists' Society 1999, 76:1143-1149.
46. Härröd M., Elfman I. Enzymatic synthesis of phosphatidylcholine with fatty acids, isooctane, carbon dioxide, and propane as solvent. Journal of the American Oil Chemists' Society 1995, 72:641-646.
47. Hassler D.F., Bell R.M. Ceramidases: enzymology and metabolic roles. Advances in Lipid Research 1993, 26:49-57.
48. Heringdorf D.M.Z., Himmel H.M., Jakobs K.H. Sphingosylphosphorylcholine - biological functions and mechanisms of action. Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids 2002, 1582:178-189.
49. Hidehiko T., Susumu H., Yuko I. Mass preparation of ceramide from fishes and shells at low costs - comprises extracting sphingomyelin or ceramide 2-aminoethyl phosphonate and eliminating phosphonic acid 1995, JP 07-265089-A.
50. Hirche F., Ulbrich-Hofmann R. The interfacial pressure is an important parameter for the rate of phospholipase D catalysed reactions in emulsion systems. Biochimica et Biophysica Acta 1999, 1436:383-389.
51. Hirche F., Ulbrich-Hofmann R. The interdependence of solvent, acceptor alcohol and enzyme source in transphosphatidylation by phospholipase D. Biocatalysis and Biotransformation 2000, 18:343-353.
52. Hirche F., Koch M.H.J., König S., Wadewitz T., Ulbrich-Hofmann R. The influence of organic solvents on phospholipid transformations by phospholipase D in emulsion systems. Enzyme and Microbial Technology 1997, 20:453-461.
53. Hosokawa M., Takahashi K., Kikuchi Y., Hatano M. Preparation of therapeutic phospholipids through porcine pancreatic phospholipase A2-mediated esterification and lipozyme-mediated acidolysis. Journal of the American Oil Chemists' Society 1995, 72:1287-1291.
54. Hosokawa M., Shimatani T., Kanada T., Inoue Y., Takahashi K. Conversion to docosahexaenoic acid-containing phosphatidylserine from squid skin lecithin by phospholipase D-mediated transphosphatidylation. Journal of Agricultural Food Chemistry 2000, 48:4550-4554.
55. Hronowski L.J.J., Szarek W.A., Hay G.W., Krebs A. Synthesis and characterization of 2-O-β-lactosylglycerol, 1,2-di-O-β-lactosyl-(R, S)-glycerols and 1,2,3-tri-O-β-lactosylglycerol. Carbohydrate Research 1991, 219:33-49.
56. Hu Y., Walker S. Remarkable structural similarities between diverse glycosyltransferases. Chemistry and Biology 2002, 9:1287-1296.
57. Huang C.-H. Mixed-chain phospholipids: structures and chain-melting behaviour. Lipids 2001, 36:1077-1097.
58. Ito M., Kurita T., Kita K. A novel enzyme that cleaves the N-acyl linkage of ceramides in various glycosphingolipids as well as sphingomyelin to produce their lyso forms. Journal of Biological Chemistry 1995, 270:24370-24374.
59. Ito M., Kurita T., Mitsutake S., Kita K. Process for the preparation of sphingolipids and sphingolipid derivatives 1999, EP 0940409A1.
60. Iwasaki Y., Mizumoto Y., Okada T., Yamamoto T., Tsutsumi K., Yamane T. An aqueous suspension system for phospholipase D-mediated synthesis of PS without toxic organic solvent. Journal of the American Oil Chemists' Society 2003, 80:653-657.
61. Jenski L.J., Zerouga M., Stillwell W. Omega-3 fatty acid-containing liposomes in cancer therapy. Proceedings of Social and Experimental Biology and Medicine 1995, 210:227-233.
62. Jorasch P., Warnecke D.C., Lindner B., Zahringer U., Heinz E. Novel processive and nonprocessive glycosyltransferases from Staphylococcus aureus and Arabidopsis thaliana synthesize glycoglycerolipids, glycophospholipids, glycosphingolipids and glycosylsterols. European Journal of Biochemistry 2000, 267:3770-3783.
63. Juneja L.R., Yamane T., Shimizu S. Studies on enzymatic conversion of phospholipids. 5. Enzymatic method of increasing phosphatidylcholine content of lecithin. Journal of the American Oil Chemists' Society 1989, 66:714-717.
64. Juneja L.R., Taniguchi E., Shimizu S., Yamane T. Increasing productivity by removing choline in conversion of phosphatidylcholine to phosphatidylserine by phospholipase-D. Journal of Fermentation and Bioengineering 1992, 73:357-361.
65. Kates M. Glycolipids, Phosphoglycolipids and Sulfoglycolipids 1990, Plenum Press, New York.
66. Kim D.S., Kim S.Y., Lee J.E., Park G.C. Skin whitening cosmetic composition containing sphingosine-1-phosphate and derivative there 2003, KR 2003087448-A.
67. Kita K., Kurita T., Ito M. Fatty acid transfer (reversed hydrolysis) and fatty acid exchange of various glycosphingolipids by sphingolipid ceramide N-deacylase 1996, 549.
68. Kita K., Kurita T., Ito M. Characterization of the reversible nature of the reaction catalyzed by sphingolipid ceramide N-deacylase. A novel form of reverse hydrolysis reaction. European Journal of Biochemistry 2001, 268:592-602.
69. Koeller K.M., Wong C. Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies. Chemical Reviews 2000, 100:4465-4493.
70. Koketsu M., Nitoda T., Sugino H., Juneja L.R., Kim M., Yamamoto T., Abe N., Kajimoto T., Wong C.-H. Synthesis of a novel sialic acid derivative (sialylphospholipid) as an antirotaviral agent. Journal of Medical Chemistry 1997, 40:3332-3335.
71. Kokusho Y., Tsunoda A., Kato S., Machida H., Iwasaki S. Production of various phosphatidylsaccharides by phospholipase-D from Actinomadura sp. strain No 362. Bioscience, Biotechnology and Biochemistry 1993, 57:1302-1305.
72. Laane C., Boeren S., Vos K., Veeger C. Rules for optimization of biocatalysis in organic solvents. Biotechnology and Bioengineering 1986, 30:81-87.
73. Lafont D., Carriere F., Ferrato F., Boullanger P. Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate. Carbohydrate Research 2006, 341:695-704.
74. Larsen E., Kharazmi A., Christensen S.B., Christensen L.P., Brandt K. Use of glycosides of mono and diacylglycerol as anti-inflammatory agents 2006, USP 7084122 B2.
75. Lasson-Backstrom C. Phospholipids containing omega-3 fatty acids 1995, USP 5434183.
76. Li X.C., Yu L.B., Zhang H., Chu S.D., Guan H.S. The synthesis of glycoglycerolipids. Chinese Chemical Letters 2003, 14:776-778.
77. Lindberg J., Svensson S., Påhlsson P., Konradsson P. Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line. Tetrahedron 2002, 58:5109-5117.
78. Mandal S.B., Sen P.C., Chakrabarti P. In vitro synthesis of phosphatidylinositol and phosphatidylcholine by phospholipase-D. Phytochemistry 1980, 19:1661-1663.
79. 3 (Edelfosine). Journal of Medicinal Chemistry 1996, 39:3241-3247.
80. Matsufuji M., Nagamatsu Y., Yoshimoto A. Protective effects of bacterial glyceroglycolipid M874B cell death caused by exposure to heat and hydrogen peroxide. Journal of Bioscience and Bioengineering 2000, 89:345-349.
81. Michaelis M., Geisslinger G., Scholich K. Use of S1 P or functional fragments or derivatives thereof for the preparation of pharmaceutical compounds 2004, EP 1481680A1.
82. Mingarro I., Abad C., Braco L. Characterization of acylating and deacylating activities of an extracellular phospholipase A2 in a water-restricted environment. Biochemistry 1994, 33:4652-4660.
83. Mitsutake S., Kita K., Okino N., Ito M. Ceramide synthesis by sphingolipid ceramide N-deacylase: new assay for ceramidase activity detection. Analytical Biochemistry 1997, 247:52-57.
84. Morigaki E., Miura Y., Takahata K., Tada M., Nakajima S., Baba N. Enzymatic preparation of sphingosine 1-phosphate. Journal of Chemical Research-S 1999, 12:774-775.
85. Morimoto T., Nagatsu A., Murakami N., Sakakibara J. Chemoenzymatic synthesis of 1-O-acyl-3-O-(6'-O-acyl-β-d-galactopyranosyl)-sn-glycerol. Tetrahedron 1995, 51:6443-6450.
86. Nagao A., Ishida N., Terao J. Synthesis of 6-phosphatidyl-L-ascorbic acid by phospholipase-D. Lipids 1991, 26:390-394.
87. Nakagawa T., Morotomi A., Tani M., Sueyoshi N., Komori H., Ito M. C18:3-GM1a induces apoptosis in Neuro2a cells: enzymatic remodelling of fatty acyl chains of glycosphingolipids. Journal of Lipid Research 2005, 46:1103-1112.
88. Nakajima N., Furuya T., Ishihara K., Matsumura S., Mizobata S., Hamada H. Enzymatic production of β-thujaplicin 2-O-β-d-glucoside in a membrane reactor using an insoluble UDP-glucosyltransferase fraction from cultured cells of Eucalyptus perriniana. Journal of Fermentation and Bioengineering 1997, 84:455-460.
89. Nakano H., Kiso T., Okamoto K., Tomita T., Manan M.B.A., Kitahata S. Synthesis of glycosylglycerol by cyclodextrin glucanotransferases. Journal of Bioscience and Bioengineering 2003, 95:583-588.
90. Okahata Y., Mori T. Biocatalytic reactions in organic media by using lipid-coated enzymes. Journal of Synthetic Organic Chemistry, Japan 1998, 11:931-939.
91. Okahata Y., Niikura K., Ijiro K. Simple transphosphatidylation of phospholipids catalyzed by a lipid-coated phospholipase-D in organic solvents 1. Journal of the Chemical Society-Perkin Transactions 1995, 7:919-925.
92. Paltauf F., Hermetter A. Strategies for the synthesis of glycerophospholipids. Progress in Lipid Research 1994, 33:239-328.
93. Park C.W., Kwon S.J., Han J.J., Rhee J.S. Transesterification of phosphatidylcholine with eicosapentaenoic acid ethyl ester using phospholipase A2 in organic solvent. Biotechnology Letters 2000, 22:147-150.
94. Pedersen K.B. Interesterification of phospholipids 2001, USP 6284501.
95. Peng L., Xu X., Mu H., Høy C.-E., Adler-Nissen J. Production of structured phospholipids by lipase-catalyzed acidolysis: optimization using response surface methodology. Enzyme and Microbial Technology 2002, 31:523-532.
96. Persson M., Svensson I., Adlercreutz P. Enzymatic fatty acid exchange in digalactosyldiacylglycerol. Chemistry and Physics of Lipids 2000, 104:13-21.
97. Pisch S., Bornscheuer U.T., Meyer H.H., Schmid R.D. Properties of unusual phospholipids. 4. Chemoenzymatic synthesis of phospholipids bearing acetylenic fatty acids. Tetrahedron 1997, 53:14627-14634.
98. Pisvejcova A., Rossi C., Husakova L., Kren V., Riva S., Monti D. β-1,4-Galactosltransferase catalysed glycosylation of sugar derivatives: Modulation of enzyme activity by α-lactalbumin, immobilization and solvent tolerance. Journal of Molecular Catalysis B: Enzymatic 2006, 39:98-104.
99. Ponting C.P., Kerr I.D. A novel family of phospholipase D homologues that includes phospholipid synthases and putative endonucleases identification of duplicated repeats and potential active-site residues. Protein Science 1996, 5:914-922.
100. Qian X., Sujino K., Palcic M.M., Ratcliffe R.M. Glycosyltransferases in oligosaccharide synthesis. Journal of Carbohydrate Chemistry 2002, 21:911-942.
101. Ramm W., Scatton W., Wagner-Dobler I., Wray V., Nimtz M., Tokuda H., Enjyo F., Nishino H., Beil W., Heckmann R., Lurtz V., Lang S. Diglucosyl-glycerolipid from the marine sponge-associated Bacillus pumilus strain AAS3: their production, enzymatic modification and properties. Applied Microbiology and Biotechnology 2004, 64:497-504.
102. Rich J.O., Khmelnitsky Y.L. Phospholipase D-catalyzed transphosphatidylation in anhydrous organic solvents. Biotechnology and Bioengineering 2001, 7:2374-2377.
103. Romeo A., Kirschner G., Menon G. Use of phosphoryl-l-serine-N-acyl-sphingosine in compositions for treating nervous system disorders and diseases involving modified immunological reactivity 1994, e.g., ischemia, trauma, Alzheimer's disease, etc, WO/1994/003178.
104. Rowan A.S., Hamilton C.J. Recent developments in preparative enzymatic syntheses of carbohydrates. Natural Product Reports 2006, 23:412-443.
105. Sakai K., Okuyama H., Yura J., Takeyama H., Shinagawa N., Tsuruga N., Kato K., Miura K., Kawase K., Tsujimura T., Naruse T., Koike L. Composition and turnover of phospholipids and neutral lipids in human breast cancer and reference tissues. Carcinogenesis 1992, 13:578-584.
106. Schäffner I., Rücknagel K.P., Mansfeld J., Ulbrich-Hofmann R. Genomic structure, cloning and expression of two-phospholipase D isoenzymes from white cabbage. European Journal of Lipid Science and Technology 2002, 104:9-87.
107. Schneider M. Phospholipids. Lipid Technologies and Applications 1997, 51-78. Marcel Dekker Inc., New York. F.D. Gunstone, F.B. Padley (Eds.).
108. Servi S. Phospholipases as synthetic catalysts. Topic of Current Chemistry 1999, 200:127-158.
109. Shigematsu Y., Hasegawa M. Process for producing egg yolk lecithin reduced PE content and/or containing substantially no impurities 1989, USP 4847015.
110. Silhavy T.J., Boos W. A convenient synthesis of (2R)-glyceryl-β-d-galactopyranoside. Journal of Biological Chemistry 1973, 248:6571-6574.
111. Smeets J.W.H., De Pater R.M., Lambers J.W.J. Enzymatic synthesis of ceramides and hybrid ceramides 1997, USP 5610040.
112. Song J.K., Han J.J., Rhee J.S. Phospholipases: Occurrence and production in microorganisms, assay for high-throughput screening, and gene discovery from natural and man-made diversity. Journal of the American Oil Chemists' Society 2005, 82:691-705.
113. Susumu H., Hidehiko T., Yumiko T. Process for preparing sphingomyelin and ceramide from erythrocyte as a starting material and a curing agent or cosmetic formulated with ceramide 1999, USP 5912152.
114. Svensson I., Adlercreutz P., Mattiasson B. Lipase-catalyzed acidolysis of phosphatidylcholine at controlled water activity. Journal of the American Oil Chemists' Society 1992, 69:986-991.
115. Takahashi K., Hosokawa M. Production of tailor-made polyunsaturated phospholipids through bioconversion. Journal of Liposome Research 2001, 11:343-353.
116. Takami M., Suzuki Y. Synthesis of novel phosphatidyldihydroxyacetone via transphosphatidylation reaction by phospholipase D. Bioscience, Biotechnology and Biochemistry 1994, 58:2136-2139.
117. Takami M., Suzuki Y. Enzymatic synthesis of novel phosphatidylgenipin and its enhanced cytotoxicity. Bioscience, Biotechnology and Biochemistry 1994, 58:1897-1898.
118. Takami M., Suzuki Y. Transphosphatidylation reaction of phosphatidylcholine to 4-methoxyphenol in water-immiscible organic-solvents with immobilized phospholipase-D. Journal of Fermentation and Bioengineering 1995, 79:313-316.
119. Takami M., Hidaka N., Miki S., Suzuki Y. Enzymatic-synthesis of novel phosphatidylkojic acid and phosphatidylarbutin, and their inhibitory effects on tyrosinase activity. Bioscience, Biotechnology and Biochemistry 1994, 58:1716-1717.
120. Takenaka F., Uchimaya H. Synthesis of α-d-glucosylglycerol by α-glucosidase and some of its characteristics. Bioscience, Biotechnology and Biochemistry 2000, 64:1821-1826.
121. Thiem J., Gambert U. Chemical transformations employing glycosyltransferases. Topics in Current Chemistry 1997, 186:21-43.
122. Tremblay P.A., Marziani F., Tino J.A.F., Pilkiewicz F.G. Enzymatic synthesis of soluble phosphatides from phospholipids 1990, WO/1991/016444.
123. Ulbrich-Hofmann R., Lerchner A., Oblozinsky M., Bezakova L. Phospholipase D and its application in biocatalysis. Biotechnology Letters 2005, 27:535-543.
124. Vaz S., Persson M., Svensson I., Adlercreutz P. Lipase catalysed fatty acid exchange in digalactosyldiacylglycerol. Improvement of the yield due to the addition of phenylboronic acid. Biocatalysis and Biotransformation 2000, 18:1-12.
125. Vessey D.A., Kelley M., Karliner J.S. A rapid radioassay for sphingosine kinase. Analytical Biochemistry 2005, 337:136-142.
126. Vikbjerg A.F., Mu H., Xu X. Parameters affecting incorporation and by-product formation during the production of structured phospholipids by lipase-catalyzed acidolysis in solvent-free system. Journal of Molecular Catalysis B-Enzymatic 2005, 36:14-21.
127. Vikbjerg A.F., Rusig J.-Y., Jonsson G., Mu H., Xu X. Strategies for production and purification of lipase-catalyzed structured phospholipids. European Journal of Lipid Science and Technology 2006, 108:802-811.
128. Vikbjerg A.F., Mu H., Xu X. Elucidation of acyl migration during lipasecatalyzed production of structured phospholipids. Journal of the American Oil Chemists' Society 2006, 83:609-614.
129. Vikbjerg A.F., Mu H., Xu X. Synthesis of structured phospholipids by immobilized PLA2 catalyzed acidolysis. Journal of Biotechnology 2007, 128:545-554.
130. Virto C., Adlercreutz P. Two-enzyme system for the synthesis of 1-lauroyl-racglycerophosphate (lysophosphatidic acid) and 1-lauroyl-dihydroxyacetonephosphate. Chemistry and Physics of Lipids 2000, 104:175-184.
131. Waite M. The PLD superfamily: insights into catalysis. Biochimica et Biophysica Acta 1999, 1439:187-197.
132. Wandzik I., Bugla J., Szeja W. Regio- and stereoselectivity in preparation of 2-deoxysugar glycoglycerolipid derivatives evaluated by high resolution 1H NMR. Chemistry and Physics of Lipids 2006, 139:77-83.
133. Wang X. Multiple forms of phospholipase D in plants: the gene family, catalytic and regulatory properties, and cellular functions. Progress of Lipid Research 2000, 39:109-149.
134. Wang P., Schuster M., Wang Y.F., Wong C.H. Synthesis of phospholipid inhibitor conjugates by enzymatic transphosphatidylation with phospholipase-D. Journal of American Chemical Society 1993, 115:10487-10491.
135. Wang X., Xu L., Zheng L. Cloning and expression of phosphatidylcholinehydrolyzing phospholipase D from Rincinus communis L. Journal of Biological Chemistry 1994, 269:20312-20317.
136. Weil M.J., Zang Y., Nair M.G. Tumor cell proliferation and cyclooxygenase inhibitory constituents in horseradish (Armoracia rusticana) and wasabi (Wasabia japonica). Journal of Agricultural Food Chemistry 2005, 53:1440-1444.
137. Yamamoto Y., Hosokawa M., Miyashita K. Production of phosphatidylcholine containing conjugated linoleic acid mediated by phospholipase A2. Journal of Molecular Catalysis B-Enzymatic 2006, 41:92-96.
138. Yamane T., Juneja L.R., Li D., Shimizu S. Enzymatic preparation of phospholipids containing various polar head groups. Annals of New York Academy for Science 1990, 613:686-690.
139. Yaqoob M., Nabi A., Masoom-Yasinzai M. Bioconversion of phosphatidylcholine to phosphatidylserine using immobilized enzyme mini-columns. Process Biochemistry 2001, 36:1181-1185.
140. Yasutake N., Totani K., Harada Y., Haraguchi S., Murata T., Usui T. Efficient synthesis of glyceroyl β-lactoside and its derivatives trough a condensation reaction by cellulase. Biochimica et Biophysica Acta 2003, 1620:252-258.
141. Yesair D.W. Method for making lysophosphatidylcholine 1998, USP 5716814.
142. Zambonelli C., Morandi P., Vanoni M.A., Tedeschi G., Servi S., Curti B., Carrea G., Di Lorenzo R., Monti D. Cloning and expression in Escherichia coli of the gene encoding Streptomyces PMF PLD, a phospholipase D with high transphosphatidylation activity. Enzyme and Microbial Technology 2003, 33:676-688.
143. Zerouga M., Stillwell W., Jenski L.J. Synthesis of a novel phosphatidylcholine conjugated to docosahexaenoic acid and methotrexate that inhibits cell proliferation. Anticancer Drugs 2002, 13:301-311.
144. Zhang L., Hellgren L.I., Xu X. Enzymatic production of ceramide from sphingomyelin. Journal of Biotechnology 2006, 123:93-105.
145. Zhang L., Hellgren L.I., Xu X. Immobilization of phospholipase C for the production of ceramide from sphingomyelin hydrolysis. Journal of the American Oil Chemists' Society 2007, 84:237-247.