Concise synthesis of the unnatural sphingosine and psychosine enantiomer

Archana R. Parameswar, Jacqueline A. Hawkins, Laurel K. Mydock, Mark S. Sands, Alexei V. Demchenko

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

The accumulation of psychosine (galactosyl sphingosine) has been associated with the pathogenesis of Krabbe disease; however, the exact mechanism, of its cytotoxicity remains unclear. Herein, we describe the synthesis of the unnatural enantiomer of erythro-sphingosine, psychosine, and related derivatives thereof that would allow for the mechanistic elucidation of the toxicity of psychosine.

Original languageEnglish
Pages (from-to)3269-3274
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
StatePublished - Jun 1 2010

Keywords

  • Carbohydrates
  • Enantioselectivity
  • Glycosylation
  • Sphingolipids

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