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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
2
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pubmed:dateCreated |
2008-2-18
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pubmed:abstractText |
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 omega-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 %.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Feb
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pubmed:issn |
1860-7187
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pubmed:author |
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pubmed:issnType |
Electronic
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pubmed:volume |
3
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
356-60
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pubmed:meshHeading |
pubmed-meshheading:18000941-Acylation,
pubmed-meshheading:18000941-Alkenes,
pubmed-meshheading:18000941-Binding Sites,
pubmed-meshheading:18000941-Chromatography, Affinity,
pubmed-meshheading:18000941-Cross-Linking Reagents,
pubmed-meshheading:18000941-Endothelial Cells,
pubmed-meshheading:18000941-Erythrocytes,
pubmed-meshheading:18000941-Humans,
pubmed-meshheading:18000941-Lysophospholipids,
pubmed-meshheading:18000941-Models, Chemical,
pubmed-meshheading:18000941-Phosphorylation,
pubmed-meshheading:18000941-Sphingosine,
pubmed-meshheading:18000941-Stereoisomerism,
pubmed-meshheading:18000941-Umbilical Veins
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pubmed:year |
2008
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pubmed:articleTitle |
Synthesis and immobilization of erythro-C14-omega-aminosphingosine-1-phosphate as a potential tool for affinity chromatography.
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pubmed:affiliation |
Global Discovery Chemistry, Novartis Institutes for BioMedical Research, Brunner Strasse 59, 1230 Wien, Austria. thomas.ullrich@novartis.com
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pubmed:publicationType |
Journal Article
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