Stereoselective Synthesis of cis-4-methylsphingosine and derivatives thereof

<strong>Background</strong><br>

Sphingosine-1-phosphate is a bioactive lipid signaling molecule and an ago-nistic ligand of five specific G protein coupled receptors named S1P1-5.These receptors play a crucial role in the cardiovascular and immune sys-tem and in angiogenesis. The known compound FTY720 (Fingolimod) is a sphingosine analogue with immunosuppressive effects and was recently approved for treatment of multiple sclerosis in the United States and Russia. The synthetic sphingosine analogue cis-4-methylsphingosine was firstly syn-thesized by R. R. Schmidt and coworkers in 1993 in nine steps. Similar to FTY720 this compound is phosphorylated in biological systems and inhibits the activity of different S1P-receptors, however the spectrum of receptors influended by cis-4-methylsphingosine is slightly different to that influenced by FTY720. Cis-4-methylsphingosine induces apoptosis of neuroblastoma cells.</p> <p><span class=“Apple-style-span“ style=“line-height: 15px; „></span></p> <p><strong>Technology</strong> <br> We offer a rapid and simple method for the stereoselective synthesis of cis-4-methylsphingosine and derivatives thereof in only two steps. The novel synthesis is characterized by using easily accessible starting material, and an overall yield of nearly 30% which is almost 100-fold compared to the synthesis known in the art. Since cis-4-methylsphingosine also influences S1P-receptors like FTY70, however with a slight different spectrum, this com-pound might have similar effects or might support or supplement the activity of FTY720. Thereby cis-4-methysphingosine has a great potential for phar-maceutical application. </p> <b>Benefits:</b> <ul> <li>Reliable, easy and rapid method for the preparation of cis-4-methylsphingosine</li> <li>Only two steps form starting material to cis-4-methylsphingosine</li> <li>Cost- and time-effective synthesis</li> <li>100-fold higher yield compared to state of the art synthesis </li> </ul><br> <div style=“margin-bottom:0cm;margin-bottom:.0001pt“><strong>IP Rights</strong></div> <div>European Patent Applic. (05/2011).<br> PCT Application (05/2012). </div> <div> </div> <div><strong>Patent Owner</strong></div> <div>Humboldt-Universität zu Berlin</div><br><br> <b>Find the technology offer and contact details here: <a href=“http://www.ipal.de/technologieangebote/10127″ target=“_blank“>http://www.ipal.de/technologieangebote/10127</a></b>

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