Detail of "2673-72-5"

Reference

Molecular arrangements in sphingolipids

Molecular arrangements in sphingolipids. Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability. Pascher, Irmin (Fac. Med., Univ. Goteborg, Goteborg, Swed.). Biochim. Biophys. Acta, 455(2), 433-51 (English) 1976. CODEN: BBACAQ. DOCUMENT TYPE: Journal CA Section: 6 (General Biochemistry) The preferred conformation of the ceramide part of sphingolipids was deduced from single crystal structures of a series of sphingolipid constituents: N-tetracosanoylphytosphingosine, glycosylphytosphingosine-HCl, sphingosine-HCl, triacetylsphingosine, DL-2-hydroxytetradecanoic acid, and N-stearoylethanolamine. The amide group of the ceramide, which serves as a link between the hydrocarbon chains, has a basic significance for the conformation of the entire mol. This rigid group, which comprises 6 atoms in a planar conformation, adopts a perpendicular orientation towards the axes of the 2 hydrocarbon chains. The carbonyl O thereby turns into an eclipsed position with the H atom at C-2 of the sphingosine. A parallel chain stacking is achieved by a sharp perpendicular bend of the fatty acid. This bend is produced by a sequence of 2 -60.degree. rotations about the C-C bonds at both sides of the . 2673-72-5 and 34839-04-8 which are cas registry numbers of chemicals are mentioned.alpha.-C atom. The orientation of the H bond donors and acceptors of the amide group and the hydroxyl groups allow lateral interaction with other lipid mols. The proposed models are supported by IR spectra, thin-layer chromatog. behavior, and monolayer studies of synthetic model ceramides. The functional role of the H bonding groups in the ceramide part of sphingolipids is emphasized and their significance for the formation of lateral H bonds within the membrane layer and thereof arising effects on membrane stability and permeability are discussed. .