350818-70-1Relevant articles and documents
Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering
Sonnenberger, Stefan,Eichner, Adina,Schmitt, Thomas,Hau?, Thomas,Lange, Stefan,Langner, Andreas,Neubert, Reinhard H.H.,Dobner, Bodo
, p. 316 - 330 (2017/06/08)
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.
Synthesis of 15N-, 13C-, and 2H-labeled methanandamide analogs
Yao, Fen-Mei,Palmer, Sonya L.,Khanolkar, Atmaram D.,Tian, Xiaoyu,Guo, Jianxin,Makriyannis, Alexandros
, p. 115 - 129 (2007/10/03)
Four isotopically labeled, metabolically stable analogs of arachidonylethanolamide (anandamide), an endogenous cannabinoid ligand, were synthesized via a five-step reaction sequence starting from arachidonic acid. These stable methanandamide derivatives will serve as probes for studying the conformational properties of anandamide in model membrane systems using solid-state NMR spectroscopy. The synthetic methods described can be applied to the preparations of other anandamide analogs with isotopic labeling in different positions of the molecule, which could be utilized in biochemical and pharmacological experiments. Copyright