D-erythro-C17-Sphingosine

This synthetic sphingosine contains an odd number of carbons with a natural D-erythro stereocenter making it an ideal internal standard for sphingolipidomic studies using HPLC and mass spectrometry. Mammalian cells contain mostly Derythro sphingosines having C18 and C20 bases with a smaller amount of C16 bases. Some bacteria and fungi have predominantly C16 or even shorter sphingosine bases. C17 sphingosine bases are easily separated by reverse phase HPLC and readily identified by mass spectrometry. They are also usually absent from, or present in low amounts in, natural systems reducing the need for background subtractions. Due to its natural stereochemistry and very similar physical characteristics to natural sphingosines this product represents the extraction and signal intensity of natural sphingosine in most applications making it a useful choice as an internal standard. This product is also active in biosynthesis and can be incorporated into more complex sphingolipids by cellular enzymes making it useful for metabolic studies. Sphingosine is the characteristic structural unit of 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 sphingosine in animal tissues. Lysosphingolipids (sphingolipids containing a free amine on carbon 3) 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 also been shown to cause an increase in the cytoplasmic calcium level of cells.