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Aziridine ring opening for the synthesis of sphingolipid analogues: Inhibitors of sphingolipid-metabolizing enzymes

AuthorsAlcaide, Anna; Llebaria, Amadeu
Issue Date2014
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 79: 2993- 3029 (2014)
AbstractA library of sphingolipid analogues is designed and tested as inhibitors against mammalian and fungal sphingolipid enzymes. The synthesis of sphingolipid analogues is based on the nucleophilic ring-opening reactions of N-activated aziridine derivatives with thiols, β-thioglycosyl thiols, phosphorothioates, phosphates, and amines to afford compounds having different lipid backbones and substituents representative of the naturally occurring sphingolipid families. The screening on mammalian sphingomyelin synthase (SMS) and glucosylceramide synthase (GCS) and yeast inositol phosphorylceramide synthase (IPCS) enzymes identified several inhibitors of GCS and IPCS, but no inhibition of SMS was observed among the tested compounds. © 2014 American Chemical Society.
Identifiersdoi: 10.1021/jo500061w
issn: 0022-3263
e-issn: 1520-6904
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