PMID: 11923095Mar 30, 2002Paper

1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol, a substrate for human sphingosine kinase

Biochimica Et Biophysica Acta
Sofie GijsbersPaul P Van Veldhoven

Abstract

The substrate specificity of human sphingosine kinase was investigated using a bacterially expressed poly(His)-tagged protein. Only the D-erythro isomer of the sphingoid bases, sphinganine and sphingenine, was effectively phosphorylated. Long chain 1-alkanols, alkane-1,2-diols, 2-amino-1-alkanol or 1-amino-2-alkanol and short chain 2-amino-1,3-alkanediols were very poor substrates, indicating that the kinase is recognizing the chain length and the position of the amino and secondary hydroxy group. A free hydroxy group at carbon 3 is not a prerequisite, however, since 1-O-hexadecyl-2-desoxy-2-amino-sn-glycerol was an efficient substrate with an apparent K(m) value of 3.8 microM (versus 15.7 microM for sphingenine). This finding opens new perspectives to design sphingosine kinase inhibitors. It also calls for some caution since it cannot be excluded that this ether lipid analogue is formed from precursors that are frequently used in research on platelet activating factor or from phospholipid analogues which are less prone to degradation.

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Citations

Apr 25, 2009·PloS One·Paola G CamolettoMaria Dolores Ledesma
Jul 19, 2015·Chemistry and Physics of Lipids·Stephanie D BoomkampNigel J Pyne
Oct 19, 2007·Biochemical and Biophysical Research Communications·Helena Van Overloop, Paul P Van Veldhoven
Dec 9, 2004·Immunology Letters·Thomas BaumrukerAndreas Billich
Aug 18, 2012·Journal of Lipids·Helena Van OverloopPaul P Van Veldhoven
May 5, 2007·Assay and Drug Development Technologies·Hiroko TogamePeter Reinemer
Sep 18, 2003·The Journal of Biological Chemistry·Andreas BillichThomas Baumruker
Nov 8, 2005·The Journal of Immunology : Official Journal of the American Association of Immunologists·Jianfei YangJun Li
Dec 16, 2020·Cancer Control : Journal of the Moffitt Cancer Center·Xianwang WangYingying Lu

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