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Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering
Author(s) -
Sonnenberger Stefan,
Eichner Adina,
Schmitt Thomas,
Hauß Thomas,
Lange Stefan,
Langner Andreas,
Neubert Reinhard H.H.,
Dobner Bodo
Publication year - 2017
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3504
Subject(s) - stratum corneum , chemistry , ceramide , deuterium , membrane , methyl group , neutron scattering , palmitic acid , neutron , organic chemistry , stereochemistry , fatty acid , alkyl , biochemistry , medicine , apoptosis , physics , pathology , quantum mechanics
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.