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Synthesis of modified and labeled acylceramides
Havrišák, Tomáš ; Opálka, Lukáš (advisor) ; Pour, Milan (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of Organic and Bioorganic Chemistry Candidate: Tomáš Havrišák Supervisor: PharmDr. Lukáš Opálka, Ph.D Title of diploma thesis: Synthesis of modified and labeled acylceramides Upper most layer of skin, stratum corneum is providing effective barrier which protects us from impact of environment. Extracellular lipids of stratum corneum are mostly composed of ceramides, free atty acids and cholesterol. Earlier it was suggested that these lipids are highly rigid, which enables sufficient barrier function. But presently, it is known that some structural parts of these lipids are more fluid. So far, ultralong ceramides (also known as acylceramides), lipids which are necessary for correct barrier function still remain partly unexplored. Mobility of sphingosine part and linoleic ester have already been studied, but mobility of the ultralong chain is speculative. Obtaining information about mobility of particular parts of acylceramides is difficult because of their unavailability with required labelling. Our aim was to prepare acylceramides with deuterium-labelled half of their ultralong chain between carbons C17 - C32 from commercially available perdeuterated compounds. From available options we chose 1,12-dibromodocecane and...
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