873802-49-4Relevant academic research and scientific papers
Synthesis and stereochemistry of ceramide B, (2S,3R,4E,6R)-N-(30-hydroxytriacontanoyl)-6-hydroxy-4-sphingenine, a new ceramide in human epidermis
Mori, Kenji,Masuda, Yui
, p. 9197 - 9200 (2003)
(2S,3R,4E,6R)-N-(30-Hydroxytriacontanoyl)-6-hydroxy-4-sphingenine (1) and its (6S)-isomer (1') were synthesized by starting from pentadecan-15-olide, the enantiomers of 1-pentadecyn-3-ol, and (S)-Garner's aldehyde. Comparison of the 1H NMR spectra of the tetraacetyl derivatives of 1 and 1' with that of ceramide B, a new protein-bound ceramide in human stratum corneum, revealed it to be (2S,3R,4E,6R)-1.
Synthesis and absolute configuration of 6-hydroxylated new ceramides in human skin, ceramides B, 4, 7 and 8
Masuda, Yui,Mori, Kenji
, p. 4789 - 4800 (2007/10/03)
6R-Configuration was assigned to three new ceramides isolated from human skin such as ceramide B [1, (2S,3R,4E,6R)-6-hydroxy-N-(30′- hydroxytriacontanoyl)-4-sphingenine], ceramide 8 [2, (2S,3R,4E,6R)-6-hydroxy-N- (tetracosanoyl)-4-sphingenine] and ceramide 4 {3, (2S,3R,4E,6R)-6-hydroxy-N- [(30′-linoleoyloxy)triacontanoyl]-4-sphingenine}. (6R,2′ R)-Configuration was given to another ceramide in human skin, ceramide 7 [4, (2S,3R,4E,6R,2′ R)-6-hydroxy-N-(2′-hydroxytetracosanoyl)-4- sphingenine]. These assignments were made possible by enzymatic preparation of the enantiomers of 1-pentadecyn-3-ol and those of 2-hydroxytetracosanoic acid. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
