Synthetic Sphingosines with C18 Sphingoid Base

Sphingosine is a characteristic structural unit of many sphingolipids such as ceramides, gangliosides, globosides, sulfatides, sphingomyelin, and others.1,2 It is most abundant in nervous tissue and cell membranes. Sphingosine with an 18-carbon chain and a double bond at carbon 4 is the most abundant isomer in animal tissues. lyso-Sphingolipids inhibit protein kinase C activity resulting in the pathogenesis of sphingolipidoses such as Krabbe's disease and Gaucher's disease.3 Sphingosine can be phosphorylated via two kinases to form sphingosine-1-phosphate, which has important signaling functions. While sphingosines and ceramides can induce apoptosis,4 sphingosine-1-phosphate can promote cell survival or proliferation. Sphingosine has been shown to cause an increase in the cytoplasmic calcium level of cells.

References:

  1. A. Merrill, Jr. “De Novo Sphingolipid Biosynthesis: A Necessary, but Dangerous, Pathway” The Journal of Biological Chemistry, Vol. 277(29) pp. 25843–25846, 2002
  2. J. Shayman “Sphingolipids” Kidney International, Vol. 58 pp. 11-26, 2000
  3. Y. Hannun and R. Bell “Lysosphingolipids inhibit protein kinase C: implications for the sphingolipidoses” Science, Vol. 235:4789 pp. 670, 1987
  4. V. Nava et al. “Sphingosine Enhances Apoptosis of Radiation-resistant Prostate Cancer Cells” Cancer Research, Vol. 60 pp. 4468-4474, 2000

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D-erythro-Sphingosine, D9