Intramolecular hydrogen bonding in cardiolipin

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DOIResolve DOI: http://doi.org/10.1016/0005-2736(91)90183-9
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TypeArticle
Journal titleBiochimica et Biophysica Acta (BBA) - Biomembranes
ISSN0005-2736
Volume1066
Issue2
Pages166174
SubjectPhospholipid; Cardiolipin; Diphosphatidylglycerol; Deoxycardiolipin; Hydrogen bonding; FTIR
AbstractFourier transform infrared (FT-IR) spectroscopy was used to determine whether intramolecular hydrogen bonding between the C-OH and P-OH groups exists in beef heart cardiolipin (CL) or in hydrogenated beef heart cardiolipin (18:0-CL) as compared to the synthetic 2′-deoxy analogue of cardiolipin (16:0-dCL). Such intramolecular hydrogen bonding would provide a structural basis for proton conduction on the molecular level. In aqueous dispersions at 20°C, both 18:0-CL and 16:0-dCL exist in the gel phase as bilayers with gel to liquid-crystalline transitions (Tm) at 61 and 56°C, respectively, whereas the unsaturated CL exists in the non-bilayer (hexagonal II) state. Evidence for intramolecular hydrogen bonding of the C-OH group in aqueous dispersions of 18:0-CL is provided by the large increase in Tm observed on changing the aqueous medium from H2O to D2O but specific hydrogen-bonded C-OH... PO2− species cannot be identified because water molecules also compete for the PO2− binding sites. However, C-OH... PO2− hydrogen bonds can be identified in dry films of the sodium salt of 18:0-CL or in CCl4 solution. In contrast, such hydrogen bonds cannot be formed in the deoxy analogue (16:0-dCL) indicating that the central C-OH group in 18:0-CL could provide a structural basis for proton conduction, involving the phosphate groups.
Publication date
PublisherElsevier Science Publishers B.V.
LanguageEnglish
AffiliationNRC Steacie Institute for Molecular Sciences; National Research Council Canada
Peer reviewedYes
NPARC number23001179
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Record identifierc2b13947-3504-4a05-bb20-5c370f4f9141
Record created2017-01-03
Record modified2017-01-03
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