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Synthesis of 7-aza- and 7-thiasphingosines, and evaluation of their interaction with sphingosine kinases and with T-cells

Mathew, Thresen and Billaud, Célia and Billich, Andreas and Cavallari, Marco and Nussbaumer, Peter and De Libero, Gennaro and Vasella, Andrea. (2009) Synthesis of 7-aza- and 7-thiasphingosines, and evaluation of their interaction with sphingosine kinases and with T-cells. Chemistry & biodiversity, Vol. 6. pp. 725-738.

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Official URL: http://edoc.unibas.ch/dok/A6005671

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Abstract

The synthesis of 7-oxasphingosine (3) and 7-oxaceramide (4) was improved by starting from the 4-methoxybenzyl-protected d-galactal 9. The sphingosine analogues 5-7 and 24 were synthesized via the azido alcohol 13. The 7-thiasphingosine 5 is a poorer substrate for both isoforms of sphingosine kinase (SPHK) than sphingosine, but showed a slight preference for SPHK2. The sulfone 6 and the 7-aza compounds 7 and 24 were not phosphorylated by either SPHK1 or SPHK2, and none of 5-7 and 24 activated invariant natural killer T (iNKT) cell clones when presented by human CD1d-transfected antigen-presenting cells (APC) or by plate-bound human CD1d. Only 7 and 24 associated with plate-bound recombinant CD1d prevented stimulation of iNKT cells by alpha-galactosylceramide (alpha-GalCer).
Faculties and Departments:03 Faculty of Medicine > Departement Biomedizin > Department of Biomedicine, University Hospital Basel > Experimental Immunology (De Libero)
UniBasel Contributors:De Libero, Gennaro
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:Helvetica Chimica Acta
ISSN:1612-1872
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:01 Feb 2013 08:46
Deposited On:01 Feb 2013 08:41

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