title: Synthesis of ceramides NS and NP with perdeuterated and specifically ω deuterated N-acyl residues.
abstract: The synthesis of 12 deuterated ceramides with either a deuteration at the last carbon atom of the amide bound fatty acid or a perdeuterated fatty acid chain is described. The ceramides were prepared starting from sphingosine or phytosphingosine and ω deuterated or perdeuterated fatty acids with PyBOP® as activating agent in high yields. For the synthesis of the specifically deuterated fatty acids, dicarboxylic acids were transformed into ω deuterated alkyl bromide, which was chain elongated with blocked ω bromo alcohols by copper catalyzed Grignard coupling. Oxidation of regenerated alcohol function yields the ω deuterated fatty acids.
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 for Medical Physics and Biophysics, Leipzig University, 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, Halle Technology and Founder's Centre GmbH, (TGZ), Halle/Saale, Germany.
authors.forename: Reinhard H H
authors.initials: RH
authors.lastname: Neubert
authors.affiliation: Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg (MLU), Halle/Saale, Germany. bodo.dobner@pharmazie.uni-halle.de.
authors.forename: Bodo
authors.initials: B
authors.lastname: Dobner
mesh_terms: D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003903:Deuterium / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D002518:Ceramides; D003903:Deuterium; C012491:phytosphingosine; D013110:Sphingosine
keywords: Grignard coupling reactions; PyBOP® coupling; ceramides; perdeuteration; stratum corneum; ω deuterated fatty acids synthesis