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Synthesis of ceramides NS and NP with perdeuterated and specifically ω deuterated N ‐acyl residues
Author(s) -
Sonnenberger Stefan,
Lange Stefan,
Langner Andreas,
Neubert Reinhard H.H.,
Dobner Bodo
Publication year - 2016
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.3443
Subject(s) - chemistry , deuterium , amide , sphingosine , alkyl , fatty acid , fatty alcohol , bromide , alcohol , organic chemistry , stereochemistry , biochemistry , physics , receptor , quantum mechanics
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.