title: Synthesis of specifically deuterated ceramide [AP]-C18 and its biophysical characterization using neutron diffraction.
abstract: The very heterogeneous group of ceramides is known to be mandatory for proper barrier functions of the outermost layer of mammalian skin, referred to as stratum corneum (SC). The synthesis of a specifically deuterated ceramide [AP]-C18 variant is described. The synthesized ceramide contains the racemic forms of the α hydroxy fatty acid. For the biophysical implementation, the received diastereomeric ceramide was applied in a neutron diffraction experiment. Therefore, a SC lipid model membrane was prepared containing the described ceramide (CER), cholesterol (CHOL), stearic acid (SA), and cholesterol sulfate (ChS) in a ratio of 55/25/15/5wt%. Thus, we were able to localize the deuterated molecule part within the bilayers. In the process, a short-periodicity phase (SPP) was observed with a unit cell scale of about 44Å. For the first time, we were able to confirm former ideas concerning the arrangement of the CER within this quaternary lipid model membrane.
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg, 06120 Halle/Saale, Germany. Electronic address: stefan.sonnenberger@pharmazie.uni-halle.de.
authors.forename: Stefan
authors.initials: S
authors.lastname: Sonnenberger
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg, 06120 Halle/Saale, Germany. Electronic address: adina.eichner@pharmazie.uni-halle.de.
authors.forename: Adina
authors.initials: A
authors.lastname: Eichner
authors.affiliation: Institute of Soft Matter and Functional Materials, Helmholtz-Zentrum Berlin für Materialien und Energie, 14109 Berlin, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Hauß
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg, 06120 Halle/Saale, Germany.
authors.forename: Annett
authors.initials: A
authors.lastname: Schroeter
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg, 06120 Halle/Saale, Germany; Institute of Applied Dermatopharmacy at the Martin Luther University Halle-Wittenberg, 06120 Halle/Saale, Germany. Electronic address: reinhard.neubert@pharmazie.uni-halle.de.
authors.forename: Reinhard H H
authors.initials: RH
authors.lastname: Neubert
authors.affiliation: Institute of Pharmacy, Martin Luther University Halle-Wittenberg, 06120 Halle/Saale, Germany.
authors.forename: Bodo
authors.initials: B
authors.lastname: Dobner
mesh_terms: D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D033363:Neutron Diffraction; D012867:Skin / Q000737:chemistry / Q000378:metabolism*
chemical_list: D002518:Ceramides; D008051:Lipid Bilayers
keywords: CER[AP]; Ceramides; Neutron diffraction; Specific deuteration; Synthesis