The importance of hydrogen bonding in sphingomyelin's membrane interactions with co-lipids

A2 Review article, Literature review, Systematic review

Internal Authors/Editors

Publication Details

List of Authors: Slotte, J.Peter
Publisher: Elsevier BV
Publication year: 2016
Journal: BBA - Biomembranes
Journal acronym: BBA MEM
Volume number: 1858
Issue number: 2
Start page: 304
End page: 310
eISSN: 1879-2642


Sphingomyelin is an important constituent of mammalian cell membranes. Its molecular structure is N-acyl-D-erythro-sphingosylphosphorylcholine. The N-acyls in sphingomyelin often contain 16-24 carbons that are mostly saturated chains; however, the monounsaturated 24:1(Δ15c) acyl chain is also common. In addition to the more saturated nature of sphingomyelins, compared to physiologically relevant glycerophospholipids, also their hydrogen bonding properties are very different from the glycerophospholipids. Sphingomyelins form extensive intramolecular hydrogen bonds (from the 3OH of the long-chain base to phosphate oxygens of the head group), but also intermolecular hydrogen bonding involving the NH of the long-chain base are important for sphingomyelin (and sphingolipid) properties in membrane environments. Hydrogen bonding involving sphingomyelin has been shown to markedly stabilize interactions with both cholesterol and ceramide in fully hydrated bilayers. Such interactions contribute to the propensity of saturated sphingomyelin to form a liquid-ordered phase together with cholesterol, or a gel phase with saturated ceramides. The purpose of this review is to present recent experimental and computational evidence in support of the importance of hydrogen bonding for the interaction of sphingomyelin with other membrane lipids.

Last updated on 2020-08-04 at 07:41