Hydrogen bonding between anhydrous cholesterol and phosphatidylcholines: an infrared spectroscopic study.
Fourier transform infrared spectroscopy performed with a high pressure diamond anvil cell was used to study hydrogen bonding between anhydrous phosphatidylcholines and cholesterol at the molar ratio 4:1. The hydroxyl group of cholesterol which acts as a proton donor, engages in strong hydrogen bonding to the sn-2 chain carbonyl group of DMPC, DPPC and HPPC and in weak hydrogen bonding to the phosphate group of all these phospholipids. No evidence of hydrogen bonding between cholesterol and the sn-1 chain carbonyl group of DMPC and DPPC was found. From a comparison of the relative hydrogen-bond strengths between cholesterol or water and the sn-2 chain carbonyl and phosphate groups of all these phospholipids, it is predicted that in aqueous dispersions of cholesterol containing phospholipids, the hydrogen bond of cholesterol to the phosphate group would be replaced by that of water, while the hydrogen bond of cholesterol to the sn-2 chain carbonyl group would remain intact.
Wong
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Division of Chemistry, National Research Council of Canada, Ottawa.
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Mantsch
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D015060:1,2-Dipalmitoylphosphatidylcholine / Q000378:metabolism; D002784:Cholesterol / Q000378:metabolism*; D004134:Dimyristoylphosphatidylcholine / Q000378:metabolism; D006860:Hydrogen Bonding; D008244:Lysophosphatidylcholines / Q000378:metabolism; D010710:Phosphates; D010713:Phosphatidylcholines / Q000378:metabolism*; D013055:Spectrophotometry, Infrared; D014867:Water
D008244:Lysophosphatidylcholines; D010710:Phosphates; D010713:Phosphatidylcholines; D014867:Water; C006065:We 201; D015060:1,2-Dipalmitoylphosphatidylcholine; D002784:Cholesterol; D004134:Dimyristoylphosphatidylcholine