Synthesis and properties of dimeric glycerophospholipid: 2,2'-dotriacontanedioylbis(1-palmitoyl-sn-glycero-3-phosphocholine).
2,2'-Dotriacontanedioylbis(1-palmitoyl-sn-glycero-3-phosphocholine ) was synthesized chemically as a dimeric version of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine. Upon sonication in water, the bipolar lipid furnished a planar membrane of about 50 Angstrom thickness with gel-to-liquid crystalline phase transition constants of Tm = 53.4 degrees C, DeltaH = 20.9 kcal/mol, and DeltaS = 64.0 e.u. In an air/water interface, the lipid displayed unique surface pressure-surface area isotherms with a limiting area of 105-190 Angstrom/molecule at 10-20 degrees C. The lipid was a substrate of phospholipase A2 (Naja mocambique), which afforded 1-palmitoyl-sn-glycero-3-phosphocholine and dotriacontanedioic acid as final products.
Department of Bioapplied Chemistry, Osaka City University, Sumiyoshi-ku.
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Yamauchi
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Togawa
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Kinoshita
D002021:Buffers; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006868:Hydrolysis; D008051:Lipid Bilayers; D008081:Liposomes / Q000737:chemistry; D010713:Phosphatidylcholines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D010741:Phospholipases A / Q000378:metabolism; D054467:Phospholipases A2; D013499:Surface Properties; D014867:Water
D002021:Buffers; D008051:Lipid Bilayers; D008081:Liposomes; D010713:Phosphatidylcholines; D014867:Water; C047037:1,2-ditetradecylphosphatidylcholine; D010741:Phospholipases A; D054467:Phospholipases A2