Premium
Synthesis and Immobilization of erythro ‐C14‐ω‐Aminosphingosine‐1‐phosphate as a Potential Tool for Affinity Chromatography
Author(s) -
Ullrich Thomas,
Ghobrial Michael,
Peters Carsten,
Billich Andreas,
Guerini Danilo,
Nussbaumer Peter
Publication year - 2008
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200700285
Subject(s) - chemistry , phosphate , regioselectivity , sphingosine 1 phosphate , acylation , derivative (finance) , diastereomer , alkyl , combinatorial chemistry , metathesis , protecting group , cleavage (geology) , stereochemistry , affinity chromatography , sphingosine , organic chemistry , biochemistry , enzyme , receptor , catalysis , polymer , geotechnical engineering , fracture (geology) , financial economics , engineering , economics , polymerization
A sphingosine‐1‐phosphate (S1P) analogue containing a terminal alkyl chain amino group is synthesized in a few steps via olefin cross‐metathesis of an optically resolved intermediate and subsequent phosphorylation. Regioselective acylation of this intermediate at its N terminus in solution is demonstrated as a model reaction and provides a biologically active derivative. Finally, the ω‐amino intermediate is immobilized on an affinity matrix. The choice of a UV‐active phosphate protecting group allows for quantification of resin loading after cleavage which amounted to 66 %.