Synthesis and Immobilization of  erythro ‐C14‐ω‐Aminosphingosine‐1‐phosphate as a Potential Tool for Affinity Chromatography | Zendy

Ullrich Thomas | Zendy; Ghobrial Michael | Zendy; Peters Carsten | Zendy; Billich Andreas | Zendy; Guerini Danilo | Zendy; Nussbaumer Peter | Zendy

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 %.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research