Conformational studies of sphingolipids by NMR spectroscopy. II. Sphingomyelin

C. Mark Talbott, Igor Vorobyov, Douglas Borchman, K. Grant Taylor, Donald B. Dupré, M. Cecilia Yappert

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

Sphingomyelin (SM) is the most prevalent sphingolipid in the majority of mammalian membranes. Proton and 31P nuclear magnetic resonance spectral data were acquired to establish the nature of intra- and intermolecular H- bonds in the monomeric and aggregated forms of SM and to assess possible differences between this lipid and dihydrosphingomyelin (DHSM), which lacks the double bond between carbons 4 and 5 of the sphingoid base. The spectral trends suggest the formation of an intramolecular H-bond between the OH group of the sphingosine moiety and the phosphate ester oxygen of the head group. The narrower linewidth and the downfield shift of the resonance corresponding to OH proton in SM suggest that this H-bond is stronger in SM than in DHSM. The NH group appears to be involved predominantly in intramolecular H-bonding in the monomer. As the concentration of SM increases and the molecules come in closer proximity, these intramolecular bonds are partially disrupted and the NH group becomes involved in lipid-water interactions. The difference between the SM and DHSM appears to be not in the nature of these interactions but rather in the degree to which these intermolecular interactions prevail. As SM molecules cannot come as close together as DHSM molecules can, both the NH and OH moieties remain, on average, more intramolecularly bonded as compared to DHSM. (C) 2000 Elsevier Science B.V.

Original languageEnglish (US)
Pages (from-to)326-337
Number of pages12
JournalBiochimica et Biophysica Acta - Biomembranes
Volume1467
Issue number2
DOIs
StatePublished - Aug 25 2000
Externally publishedYes

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Sphingolipids
Sphingomyelins
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Molecules
Protons
Lipids
Sphingosine
Linewidth
Esters
Carbon
Monomers
Phosphates
Nuclear magnetic resonance
Oxygen
Membranes
Water

Keywords

  • Conformation
  • H-bonding
  • Lipid-lipid interaction
  • Nuclear magnetic resonance
  • Sphingolipid
  • Sphingomyelin

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Cell Biology

Cite this

Conformational studies of sphingolipids by NMR spectroscopy. II. Sphingomyelin. / Talbott, C. Mark; Vorobyov, Igor; Borchman, Douglas; Taylor, K. Grant; Dupré, Donald B.; Yappert, M. Cecilia.

In: Biochimica et Biophysica Acta - Biomembranes, Vol. 1467, No. 2, 25.08.2000, p. 326-337.

Research output: Contribution to journalArticle

Talbott, C. Mark ; Vorobyov, Igor ; Borchman, Douglas ; Taylor, K. Grant ; Dupré, Donald B. ; Yappert, M. Cecilia. / Conformational studies of sphingolipids by NMR spectroscopy. II. Sphingomyelin. In: Biochimica et Biophysica Acta - Biomembranes. 2000 ; Vol. 1467, No. 2. pp. 326-337.
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