Application Notes:
3-keto-Dihydrosphingosine is a vital intermediate in the biosynthesis of ceramides.1,2 This lyso-sphingolipid is formed by the
condensation of L-serine and palmitoyl-CoA by the serine palmitoyl transferase enzyme.3 It is then reduced to
dihydrosphingosine, converted to ceramide, and eventually synthesized into many types of sphingolipids. C18-ketodihydrosphingosine
is the major sphingolipid precursor in the early and intermediate stages of cell life with C20-ketodihydrosphingosine
as a minor component. Towards the end of the cell’s life the ratio of C18 to C20 ketodihydrosphingosine
becomes more equal. It seems to be a critical regulating step in the availability of sphingolipids in cells.
Vitamin K deficiency results in the inactivation of the serine palmitoyl transferase enzyme causing a resultant shortage of
sphingolipids. Short-chain analogs of 3-keto-dihydrosphingosine have different physical properties from the long-chain 3-
keto-dihydrosphingosines. Short-chain bases are considerably less hydrophobic which could significantly change the process
of signal transduction.
References:
1. N. Bartke and Y. Hannun “Bioactive sphingolipids: metabolism and function” Journal of Lipid Research, Vol. 50 pp. S91-S96, 2009
2. G. Jenkins and Y. Hannun “Role for de Novo Sphingoid Base Biosynthesis in the Heat-induced Transient Cell Cycle Arrest of Saccharomyces cerevisiae”
Journal of Biological Chemistry, Vol. 276 pp. 8574-8581, 2001
3. A. Batheja et al. “Characterization of Serine Palmitoyltransferase in Normal Human Tissues” Journal of Histochemistry and Cytochemistry, Vol. 51 pp.
687-696, 2003