Synthesis and Immobilization of erythro-C14-ω-Aminosphingosine-1-phosphate as a Potential Tool for Affinity Chromatography
✍ Scribed by Thomas Ullrich; Michael Ghobrial; Carsten Peters; Andreas Billich; Danilo Guerini; Peter Nussbaumer
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 210 KB
- Volume
- 3
- Category
- Article
- ISSN
- 1860-7179
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✦ Synopsis
Abstract
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 %.