title: Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering.
abstract: The synthesis of specific deuterated derivatives of the long chained ceramides [EOS] and [EOP] is described. The structural differences with respect to the natural compounds are founded in the substitution of the 2 double bonds containing linoleic acid by a palmitic acid branched with a methyl group in 10-position. The specific deuteration is introduced both in the branched and in the terminal methyl group, which was realized by common methods of successive deuteration of carboxylic groups in 3 steps. These modified fatty acids resp. the corresponding ceramides [EOS] and [EOP] were prepared for neutron scattering investigations. First results of these investigations were presented in this manuscript showing that the deuterated compounds could be detected in the stratum corneum lipid model membranes. The deuterated ceramides [EOS] and [EOP] are valuable tools to investigate the influence of these long chained ceramide species on the nanostructure of stratum corneum lipid model membranes.
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg (MLU), Halle (Saale), Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Sonnenberger
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg (MLU), Halle (Saale), Germany.
authors.forename: Adina
authors.initials: A
authors.lastname: Eichner
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg (MLU), Halle (Saale), Germany.|Institute of Applied Dermatopharmacy, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Schmitt
authors.affiliation: Institute of Soft Matter and Functional Materials, Helmholtz-Zentrum Berlin für Materialien und Energie, Berlin, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Hauß
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg (MLU), Halle (Saale), Germany.|Institute for Medical Physics and Biophysics, University Leipzig, Leipzig, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Lange
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg (MLU), Halle (Saale), Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Langner
authors.affiliation: Institute of Applied Dermatopharmacy, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Reinhard H H
authors.initials: RHH
authors.lastname: Neubert
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg (MLU), Halle (Saale), Germany.
authors.forename: Bodo
authors.identifier: 0000-0002-0397-4818
authors.initials: B
authors.lastname: Dobner
mesh_terms: D002462:Cell Membrane / Q000737:chemistry; D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003903:Deuterium / Q000737:chemistry*; D000078404:Epidermal Cells; D004817:Epidermis / Q000737:chemistry*; D033363:Neutron Diffraction
chemical_list: D002518:Ceramides; D003903:Deuterium
keywords: CER[EOP]; CER[EOS]; branched fatty acid; neutron scattering investigations; specific deuteration