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Synthesis of an inhibitor of sphingosine-1-phosphate lyase

✍ Scribed by Ahcene Boumendjel; Stephen P.F. Miller

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
318 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

The 24nyl ~hy~~~l-~~ 1. was syatbe&i and testesI for i~ibi~ of ~~~-~ Iyase. The carboo akeletoa was wepared by acylacion of a methioaiae imine with N-metboxy-N-methyl palmitatnide. The vinyl group was generated by thermal sulbxide eliiination. Reduction of both carbonyl groups and &protection gave P-vinyl dihydrosphingosine. The phosphate group was intruduced by means of bis(2-cyanoethyl)-N,Nv-diisopropyl-phospltoramidite as monofunctional phosphitylation reagent. Sphmgolipids constitnte a large class of biologicaly important compo~&. Both glycosldes (cerebrosides, gangliosides) and non-glyccsylated derivatives (sphingomyelin, ceramides) are imporumt constituents of cellular membranes 1. The principal component of sphingolipids is almost invariably the long chain base, sphingosine. Kecently several reparts have shown sphiigosine to be a potent inhibitor of the regulatory enzyme pnxein kinase C (PKC) both in vlvo and ia V&V 2-In additiou sphingosine-l-phosphate causes rapid mtnslocation of calcium f-mm intracelh~ku stores and a regulatory role has been suggested for this compound 3.

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