{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T21:32:16Z","timestamp":1791408736223,"version":"4.3.3"},"reference-count":105,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2010,3,8]],"date-time":"2010-03-08T00:00:00Z","timestamp":1268006400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>New synthetic methods for the preparation of biologically active phospholipids and lysophospholipids (LPLs) are very important in solving problems of membrane\u2013chemistry and biochemistry. Traditionally considered just as second-messenger molecules regulating intracellular signalling pathways, LPLs have recently shown to be involved in many physiological and pathological processes such as inflammation, reproduction, angiogenesis, tumorogenesis, atherosclerosis and nervous system regulation. Elucidation of the mechanistic details involved in the enzymological, cell-biological and membrane-biophysical roles of LPLs relies obviously on the availability of structurally diverse compounds. A variety of chemical and enzymatic routes have been reported in the literature for the synthesis of LPLs: the enzymatic transformation of natural glycerophospholipids (GPLs) using regiospecific enzymes such as phospholipases A1 (PLA1), A2 (PLA2) phospholipase D (PLD) and different lipases, the coupling of enzymatic processes with chemical transformations, the complete chemical synthesis of LPLs starting from glycerol or derivatives. In this review, chemo-enzymatic procedures leading to 1- and 2-LPLs will be described.<\/jats:p>","DOI":"10.3390\/molecules15031354","type":"journal-article","created":{"date-parts":[[2010,3,8]],"date-time":"2010-03-08T11:22:08Z","timestamp":1268047328000},"page":"1354-1377","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":145,"title":["Synthesis of Lysophospholipids"],"prefix":"10.3390","volume":"15","author":[{"given":"Paola","family":"D\u2019Arrigo","sequence":"first","affiliation":[{"name":"Dipartimento di Chimica, Materiali ed Ingegneria Chimica \u201cGiulio Natta\u201d, Politecnico di Milano, Via Mancinelli 7, 20131 Milano, Italy"},{"name":"Centro Interuniversitario di Ricerca in Biotecnologie Proteiche \"The Protein Factory\", Politecnico di Milano and Universit\u00e0 degli Studi dell'Insubria, Via Mancinelli 7, 20131 Milano, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefano","family":"Servi","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica, Materiali ed Ingegneria Chimica \u201cGiulio Natta\u201d, Politecnico di Milano, Via Mancinelli 7, 20131 Milano, Italy"},{"name":"Centro Interuniversitario di Ricerca in Biotecnologie Proteiche \"The Protein Factory\", Politecnico di Milano and Universit\u00e0 degli Studi dell'Insubria, Via Mancinelli 7, 20131 Milano, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2010,3,8]]},"reference":[{"key":"ref_1","unstructured":"Vance, D.E., and Vance, J.E. (2002). Biochemistry of Lipids, Lipoproteins and membranes, Elsevier Science. [4th ed.]."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/S1874-5245(97)80006-7","article-title":"The role of phospholipids in cell function","volume":"2","author":"Dowhan","year":"1997","journal-title":"Adv. Lipobiol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"10073","DOI":"10.1021\/jo034843v","article-title":"Synthesis and supramolecolar properties of conformationally restricted and flexible phospholipids","volume":"68","author":"Vares","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Baskin, A., and Norde, W. (2000). Physical Chemistry of Biological Interfaces, Marcel Dekker.","DOI":"10.1201\/9781482293227"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1589","DOI":"10.1096\/fasebj.12.15.1589","article-title":"Diversity of cellular receptors and functions for the lysophospholipid growth factors lysophosphatidic acid and sphingosine 1-phosphate","volume":"12","author":"Goetzl","year":"1998","journal-title":"FASEB J."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1146\/annurev.biochem.66.1.199","article-title":"Molecular basis for membrane phospholipids diversity: Why are there so many phospholipids","volume":"66","author":"Dowhan","year":"1997","journal-title":"Ann. Rev. Biochem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5471","DOI":"10.1021\/la991711h","article-title":"Histidine-tagged amphiphiles for the reversible formation of lipid bilayer aggregates on chelator-functionalized gold surfaces","volume":"16","author":"Stora","year":"2000","journal-title":"Langmuir"},{"key":"ref_8","first-page":"9","article-title":"Current trends in the production and biomedical applications of liposomes: A review","volume":"4","author":"Uhumwangho","year":"2005","journal-title":"J. Med. Biomed. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1016\/S0169-409X(96)00476-0","article-title":"Long-circulating liposomes for drug delivery in cancer therapy: A review of biodistribution in tumor-bearing animals","volume":"24","author":"Gabizon","year":"1997","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_10","unstructured":"Cevc, G., and Paltauf, F. (1995). Phospholipids: Characterization, Metabolism, and Novel Biological Applications, AOCS Press."},{"key":"ref_11","unstructured":"Dennis, E.A., Brown, H.A., Deems, R.A., Glass, C.K., Merrill, A.H., Murphy, R.C., Raetz, C.R.H., Shaw, W., Subramaniam, S., Russell, D.W., VanNieuwenhze, M.S., White, S.H., Witztum, J.L., and Wooley, J. (2006). Functional lipodomics, CRC Press."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2695","DOI":"10.1007\/s00018-006-6155-y","article-title":"New developments in the biological functions of lysophospholipids","volume":"63","author":"Birgbauer","year":"2006","journal-title":"Cell. Mol. Life Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1111\/j.1749-6632.2000.tb06532.x","article-title":"Development of our current understanding of bioactive lysophospholipids","volume":"905","author":"Moolenaar","year":"2000","journal-title":"Ann. N. Y. Acad. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1134\/S0006297907020010","article-title":"Lysophospholipids receptors in cell signaling","volume":"72","author":"Torkhovskaya","year":"2007","journal-title":"Biochemistry (Moscow)"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1016\/j.bbalip.2008.04.011","article-title":"Lysophospholipid interactions with protein targets","volume":"1781","author":"Parrill","year":"2008","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1095","DOI":"10.1002\/jcb.20129","article-title":"Mechanisms of cardioprotection by lysophospholipids","volume":"92","author":"Karliner","year":"2004","journal-title":"J. Cell. Biochem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1016\/j.prostaglandins.2004.09.009","article-title":"Lysophospholipids in the nervous system","volume":"77","author":"Chun","year":"2005","journal-title":"Prostaglandins Other Lipid Mediat."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/j.molmed.2005.12.001","article-title":"Emerging medicinal roles for lysophospholipid signalling","volume":"12","author":"Gardell","year":"2006","journal-title":"Trends Mol. Med."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"582","DOI":"10.1038\/nrc1143","article-title":"The emerging role of lysophosphatidic acid in cancer","volume":"3","author":"Mills","year":"2003","journal-title":"Nat. Rev. Cancer"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"7983","DOI":"10.1158\/0008-5472.CAN-05-4381","article-title":"Hypoxia enhances lysophosphatidic acid responsiveness in ovarian cancer cells and lysophosphatidic acid induces ovarian tumor metastasis in vivo","volume":"66","author":"Kim","year":"2006","journal-title":"Cancer Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1001\/jama.280.8.719","article-title":"Lysophosphatidic acid as a potential biomarker for ovarian and other gynecologic cancers","volume":"280","author":"Xu","year":"1998","journal-title":"J. Am. Med. Assoc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1185","DOI":"10.1158\/1055-9965.1185.13.7","article-title":"Lysophospholipids are potential biomarkers of ovarian cancer","volume":"13","author":"Sutphen","year":"2004","journal-title":"Cancer Epidemiol. Biomarkers Prev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2696","DOI":"10.1200\/JCO.2006.08.5571","article-title":"Plasma lysophosphatidylcholine levels: Potential biomarkers for colorectal cancer","volume":"25","author":"Zhao","year":"2007","journal-title":"J. Clin. Oncol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/j.patbio.2004.01.005","article-title":"Lysophospholipids and cancer: Current status and perpespectives","volume":"53","author":"Raynal","year":"2005","journal-title":"Pathol. Biol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"27090","DOI":"10.1074\/jbc.271.43.27090","article-title":"The Bioactive phospholipid, lysophosphatidylcholine, induces cellular effects via G-protein-dependent activation of adenylyl cyclase","volume":"271","author":"Yan","year":"1996","journal-title":"J. Biol. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1007\/s11745-999-332-5","article-title":"Abnormal serum lysophospholipids in multiple myeloma patients","volume":"34","author":"Sasagawa","year":"1999","journal-title":"Lipids"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"754","DOI":"10.1194\/jlr.M200401-JLR200","article-title":"Plasma ceramide and lysophosphatidylcholine inversely correlate with mortality in sepsis patients","volume":"44","author":"Drobnik","year":"2003","journal-title":"J. Lipid Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"925","DOI":"10.1016\/j.clinbiochem.2005.06.006","article-title":"The phosphatidylcholine\/lysophosphatidylcholine ratio in human plasma is an indicator of the severity of rheumatoid arthritis: Investigations by 31P NMR and MALDI-TOF MS","volume":"38","author":"Fuchs","year":"2005","journal-title":"Clin. Biochem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1080\/00365520410006233","article-title":"Phosphatidylcholine and lysophosphatidylcholine in intestinal mucus of ulcerative colitis patients. A quantitative approach by nano Electrospray-tandem mass spectrometry","volume":"39","author":"Ehehalt","year":"2004","journal-title":"Scand. J. Gastroenterol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.jchromb.2006.03.006","article-title":"Quantification of lysophosphatidylcholines and phosphatidylcholines using liquid chromatography-tandem mass spectrometry in neonatal serum","volume":"838","author":"Takatera","year":"2006","journal-title":"J. Chromatogr. B Analyt. Technol. Biomed. Life Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"161","DOI":"10.2174\/138161206775193109","article-title":"Lysophospholipid receptors as potential drug targets in tissue transplantation and autoimmune diseases","volume":"12","author":"Chun","year":"2006","journal-title":"Curr. Pharm. Des."},{"key":"ref_32","first-page":"31","article-title":"Effect of lysophosphatidylcholine on transmembrane signal transduction","volume":"63","author":"Prokazova","year":"1998","journal-title":"Biochemistry (Moscow)"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"511","DOI":"10.1189\/jlb.0402179","article-title":"Lysophosphatidylcholines prime the NADPH oxidase and stimulate multiple neutrophil functions through changes in cytosolic calcium","volume":"73","author":"Silliman","year":"2003","journal-title":"J. Leucoc. Biol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"716","DOI":"10.1073\/pnas.90.2.716","article-title":"Possible role of mammalian secretory group II phospholipase A2 in T-lymphocyte activation: implication in propagation of inflammatory reaction","volume":"90","author":"Asaoka","year":"1993","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1391","DOI":"10.1006\/jmcc.1999.0973","article-title":"Lysophosphatidylcholine, a metabolite which accumulates early in myocardium during ischemia, reduces gap junctional coupling in cardiac cells","volume":"31","author":"Daleau","year":"1999","journal-title":"J. Mol. Cell. Cardiol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1209","DOI":"10.1042\/bst0311209","article-title":"Lysophosphatidic acid: Mitogen and motility factor","volume":"31","author":"Giepsmans","year":"2003","journal-title":"Biochem. Soc. Trans."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"12949","DOI":"10.1074\/jbc.270.22.12949","article-title":"Lysophosphatidic acid, a multifunctional phospholipid messenger","volume":"270","author":"Moolenar","year":"1995","journal-title":"J. Biol. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"870","DOI":"10.1002\/bies.20081","article-title":"The ins and outs of lysophosphatidic acid signalling","volume":"26","author":"Moolenaar","year":"2004","journal-title":"Bioassays"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"23","DOI":"10.2174\/1568005310303010023","article-title":"Unfolding the pathophysiological role of bioactive lysophospholipids","volume":"3","author":"Xu","year":"2003","journal-title":"Curr. Drug Targets Immune Endocr. Metabol. Disord."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"216","DOI":"10.1016\/S1388-1981(02)00174-9","article-title":"Lysophospholipids and the cardiovascular system","volume":"1582","author":"Karliner","year":"2002","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"503","DOI":"10.1016\/j.semcdb.2004.05.003","article-title":"Biology of LPA in health and disease","volume":"15","author":"Sengupta","year":"2004","journal-title":"Semin. Cell Dev. Biol."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3006","DOI":"10.1158\/0008-5472.CAN-05-1292","article-title":"Lysophosphatidic acid is constitutively produced by human peritoneal mesothelial cells and enhances adhesion, migration, and invasion of ovarian cancer cells","volume":"66","author":"Ren","year":"2006","journal-title":"Cancer Res."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1017\/S1462399407000476","article-title":"Targeting the lipids LPA and S1P and their signaling pathways to inhibit tumour progression","volume":"9","author":"Murph","year":"2007","journal-title":"Expert Rev. Mol. Med."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3109\/10242420009040119","article-title":"Lipase-catalyzed fatty acid exchange in digalactosyldiacylglycerol. Improvement of yield due to the addition of phenylboronic acid","volume":"18","author":"Vaz","year":"2000","journal-title":"Biocatal. Biotransfor."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1002\/bit.10225","article-title":"Synthesis of Phosphatidylcholine with defined fatty acid in the sn-1 position by lipase-catalyzed esterification and transesterification reaction","volume":"78","author":"Adlercreutz","year":"2002","journal-title":"Biotechnol. Bioeng."},{"key":"ref_46","unstructured":"Cevc, G. (1995). Phospholipids Handbook, Marcel Dekker."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1016\/S0957-4166(97)00371-6","article-title":"The stereospecific synthesis of mixed-acid phospholipids with polyunsaturated fatty acid from D-mannitol","volume":"8","author":"Xia","year":"1997","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1021\/jo010734+","article-title":"Efficient synthesis of phospholipids from glycidyl phosphates","volume":"67","author":"Lindberg","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"5875","DOI":"10.1016\/S0040-4039(03)01419-9","article-title":"A new approach to the synthesis of lysophosphatidylcholines and related derivatives","volume":"44","author":"Bibak","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"7371","DOI":"10.1016\/j.tetlet.2004.07.161","article-title":"A new approach to the synthesis of lysophospholipids: Preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenylglycerate","volume":"45","author":"Rossetto","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1691","DOI":"10.1021\/jo062352f","article-title":"A new synthesis of lysophosphatidylcholines and related derivatives. Use of p-toluensulfonate for hydroxyl Group Protection","volume":"72","author":"Rossetto","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1394","DOI":"10.1021\/ja01184a031","article-title":"L-alfa-Glycerylphosphorylcholine","volume":"70","author":"Baer","year":"1948","journal-title":"J. Am. Chem. Soc."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/0009-3084(70)90067-8","article-title":"Preparation of crystalline L-alfa-glycerophosphorylcholine-cadmium chloride adduct from commercial egg lecithin","volume":"4","author":"Chada","year":"1970","journal-title":"Chem. Phys. Lipids"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1016\/j.chemphyslip.2005.06.001","article-title":"Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine","volume":"137","author":"Ichihara","year":"2005","journal-title":"Chem. Phys. Lipids"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2974","DOI":"10.1039\/b604636c","article-title":"Tin-mediated synthesis of lyso-phospholipids","volume":"4","author":"Fasoli","year":"2006","journal-title":"Org. Biomol. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/j.chemphyslip.2007.03.008","article-title":"A practical selective synthesis of mixed short\/long chains glycerophosphocholines","volume":"147","author":"Fasoli","year":"2007","journal-title":"Chem. Phys. Lipids"},{"key":"ref_57","unstructured":"Dennis, E.A. (1991). Methods in Enzymology, Academic Press, Inc."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1016\/S0167-7799(97)01012-3","article-title":"Using phospholipases for phospholipid modification","volume":"15","author":"Servi","year":"1997","journal-title":"Trends Biotech."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/S0009-3084(99)00025-0","article-title":"Phospholipase D structure and regulation","volume":"98","author":"Frohman","year":"1999","journal-title":"Chem. Phys. Lipids"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1093\/oxfordjournals.jbchem.a003101","article-title":"Signaling phospholipase A2","volume":"131","author":"Murakami","year":"2002","journal-title":"J. Biochem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1006\/jmbi.1997.1490","article-title":"Structural and mechanistic comparison of prokaryotic and eukaryiotic phosphoinositide-specific phospholipase C","volume":"275","author":"Heinz","year":"1998","journal-title":"J. Mol.Biol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/B978-0-12-024916-9.50011-1","article-title":"Phospholipase D","volume":"16","author":"Heller","year":"1978","journal-title":"Adv. Lipid Res."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"181","DOI":"10.3109\/10242429408992119","article-title":"Modification of phospholipids with lipases and phospholipases","volume":"9","author":"Mustranta","year":"1994","journal-title":"Biocatalysis"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1007\/3-540-68116-7_5","article-title":"Phospholipases as synthetic catalysts","volume":"200","author":"Servi","year":"1999","journal-title":"Top. Curr. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","unstructured":"Bornscheuer, U.T. (2000). Enzymes in Lipid Modification, Wiley-VCH.","DOI":"10.1002\/3527606033"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1002\/ejlt.200300832","article-title":"Enzymatic fatty acid exchange in glycerophospholipids","volume":"105","author":"Adlercreutz","year":"2003","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1130","DOI":"10.1016\/j.enzmictec.2006.08.018","article-title":"Phospholipase A1-catalyzed synthesis of phospholipids enriched in \u03c9-3-polyunsaturated fatty acid residues","volume":"40","author":"Kim","year":"2007","journal-title":"Enzyme Microb. Technol."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1007\/BF02542611","article-title":"The hydrolysis of phosphatidylcholine by an immobilized lipase: Optimization of hydrolysis in organic solvents","volume":"70","author":"Haas","year":"1993","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2487","DOI":"10.1016\/S0040-4039(00)60448-3","article-title":"Regiospecific deacylation of glycerophospholipids by use of Mucor javanicus lipase","volume":"34","author":"Morimoto","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1007\/BF02533261","article-title":"Preparation of choline and ethanolamine plasmalogens by enzymatic hydrolysis of the accompanying diacyl analogs","volume":"13","author":"Paltauf","year":"1978","journal-title":"Lipids"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/0009-3084(70)90059-9","article-title":"Hydrolysis of phosphoglycerides by purified lipase preparations I. Substrate-, positional- and stereo-specificity","volume":"4","author":"Slotboom","year":"1970","journal-title":"Chem. Phys. Lipids"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1920","DOI":"10.1016\/S0021-9258(19)77966-6","article-title":"On the substrate specificity of rat liver phospholipase A1","volume":"263","author":"Kucera","year":"1988","journal-title":"J. Biol. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"499","DOI":"10.1007\/BF02663821","article-title":"Production of medium-chain glycerides by immobilized lipase in a solvent-free system","volume":"68","author":"Kim","year":"1991","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"519","DOI":"10.1007\/BF02638851","article-title":"The Enzymatic hydrolysis of triglyceride-phospholipid mixtures in an organic solvent","volume":"72","author":"Haas","year":"1995","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/0922-338X(90)90158-S","article-title":"The Enzymatic acyl exchange of phospholipids with Lipases","volume":"69","author":"Yagi","year":"1990","journal-title":"J. Ferment. Bioeng."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"483","DOI":"10.1007\/BF02540658","article-title":"Enzymatic phosphatidylcholine hydrolysis in organic solvents: An examination of selected commercially available lipases","volume":"71","author":"Haas","year":"1994","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S1388-1981(00)00105-0","article-title":"The expanding superfamily of phospholipase A2 enzymes: Classification and characterization","volume":"1488","author":"Six","year":"2000","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1016\/S0141-0229(01)00447-1","article-title":"Production of egg yolk lysolecithin with immobilized phospholipase A2","volume":"29","author":"Kim","year":"2001","journal-title":"Enzyme Microb. Technol."},{"key":"ref_79","first-page":"49","article-title":"Characterization and optimization of phospholipase A2 catalyzed synthesis of phosphatidylcholine","volume":"1259","author":"Egger","year":"1995","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1016\/S0141-0229(02)00147-3","article-title":"Production of structurated phospholipids by lipase-catalyzed acidolysis: Optimization using surface response methodology","volume":"31","author":"Peng","year":"2002","journal-title":"Enzyme Microb. Technol."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1007\/BF02541478","article-title":"Lipase-catalyzed synthesis of lyso-PLs in a continuous bioreactor","volume":"71","author":"Sarney","year":"1994","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1016\/0009-3084(91)90041-9","article-title":"Regioselective and stereoselective enzymatic esterification of glycerol and its derivatives","volume":"60","author":"Mazur","year":"1991","journal-title":"Chem. Phys. Lipids"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1111\/j.1749-6632.1998.tb10335.x","article-title":"Lipase-catalysed synthesis of lysophosphatidylcholine","volume":"864","author":"Kim","year":"1998","journal-title":"Ann. N.Y. Acad. Sci."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"630","DOI":"10.1016\/S0141-0229(00)00147-2","article-title":"Lysophosphatidylcholine synthesis with Candida Antarctica lipase B (Novozyme 435)","volume":"26","author":"Virto","year":"2000","journal-title":"Enzyme Microb. Technol."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/0304-4165(93)90088-P","article-title":"Improved purification and characterization of phospholipase D from cabbage","volume":"1158","author":"Abousalam","year":"1993","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"903","DOI":"10.1093\/oxfordjournals.pcp.a078837","article-title":"Purification and characterization of phospholipase D (PLD) from rice (Oryza sativa L.) and cloning of cDNA for PLD from rice and maize (Zea mays L.)","volume":"36","author":"Ueki","year":"1995","journal-title":"Plant Cell Physiol."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"20312","DOI":"10.1016\/S0021-9258(17)31993-2","article-title":"Cloning and expression of phosphatidylcholine-hydrolyzing phospholipase D from Ricinus communis L","volume":"269","author":"Wang","year":"1994","journal-title":"J. Biol. Chem."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1007\/s10529-005-3251-2","article-title":"Phospholipase D and its application in biocatalysis","volume":"27","author":"Lerchner","year":"2005","journal-title":"Biotech. Lett."},{"key":"ref_89","first-page":"23","article-title":"Silica-immobilized phospholipase D from Daucus carota","volume":"8","author":"Madoery","year":"1997","journal-title":"Inf. Technol."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1016\/0005-2760(94)00241-P","article-title":"Purification and properties of two phospholipases D from Streptomyces sp","volume":"1255","author":"Carrea","year":"1995","journal-title":"Biochim. Biophys. Acta."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"1083","DOI":"10.1023\/A:1018432325123","article-title":"Purification and applications of a phospholipase D from a new strain of Streptomyces","volume":"19","author":"Carrea","year":"1997","journal-title":"Biotech. Lett."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"251","DOI":"10.3109\/10242429709003193","article-title":"On the kinetic mechanism of phospholipase D from Streptomyces sp. in an emulsion system","volume":"15","author":"Carrea","year":"1997","journal-title":"Biocatal. Biotransfor."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"417","DOI":"10.1016\/0922-338X(95)91254-3","article-title":"Extracellular production of phospholipase D of Streptomyces antibioticus using recombinant Escherichia coli","volume":"79","author":"Iwasaki","year":"1995","journal-title":"J. Ferment. Bioeng."},{"key":"ref_94","first-page":"1189","article-title":"Purification and Properties of Phospholipase D from Streptomyces lydicus","volume":"54","author":"Shimbo","year":"1990","journal-title":"Agric. Biol. Chem."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1093\/oxfordjournals.jbchem.a132334","article-title":"Purification of Streptomyces chromofuscus phospholipase D by hydrophobic affinity chromatography on palmitoyl cellulose","volume":"85","author":"Imamura","year":"1979","journal-title":"J. Biochem."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"10487","DOI":"10.1021\/ja00076a004","article-title":"Synthesis of phospholipid inhibitor conjugates by enzymatic transphosphatidylation with phospholipase-D","volume":"115","author":"Wang","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1002\/ejlt.200390060","article-title":"Enzyme-catalyzed transphosphatidylation","volume":"105","year":"2003","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1016\/0898-6568(95)00076-3","article-title":"Phosphatidic Acid: a lipid messenger involved in intracellular and extracellular signalling","volume":"8","author":"English","year":"1996","journal-title":"Cell Signal"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1016\/S0021-9258(18)96298-8","article-title":"Transphosphatidylation by Phospholipase D","volume":"242","author":"Yang","year":"1967","journal-title":"J. Biol. Chem."},{"key":"ref_100","doi-asserted-by":"crossref","unstructured":"D'Arrigo, P., deFerra, L., Piergianni, V., Ricci, A., Scarcelli, D., and Servi, S. (1994). Phospholipase D from Streptomyces catalyses the transfer of secondary alcohols. J. Chem. Soc. Chem. Commun., 1709\u20131710.","DOI":"10.1039\/c39940001709"},{"key":"ref_101","first-page":"466","article-title":"Crystallization and preliminary X-ray diffraction studies of Phospholipase D from Streptomyces sp","volume":"D56","author":"Leiros","year":"2000","journal-title":"Acta Crystallogr."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"655","DOI":"10.1016\/S0969-2126(00)00150-7","article-title":"The first crystal structure of a phospholipase D","volume":"8","author":"Leiros","year":"2000","journal-title":"Structure"},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"2575","DOI":"10.1021\/ol060773d","article-title":"synthesis and evaluation of fluorogenic substrates for phospholipase D and phospholipase C","volume":"8","author":"Rose","year":"2006","journal-title":"Org. Lett."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1042\/bj1020221","article-title":"The action of the cabbage-leaf phospholipase D upon lysolecithin","volume":"102","author":"Long","year":"1967","journal-title":"Biochem. J."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/S0009-3084(00)00130-4","article-title":"Hydrolytic and transphosphatidylation activities of phospholipase D from Savoy cabbage towards lysophosphatidylcholine","volume":"106","author":"Virto","year":"2000","journal-title":"Chem. Phys. Lipids"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/15\/3\/1354\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T22:01:39Z","timestamp":1760220099000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/15\/3\/1354"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,3,8]]},"references-count":105,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2010,3]]}},"alternative-id":["15031354"],"URL":"https:\/\/doi.org\/10.3390\/molecules15031354","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,3,8]]}}}