A type 2 Ferrier rearrangement-based synthesis of D-myo-inositol 1,4,5-trisphosphate

Neil S. Keddie, Geert Bultynck, Tomas Luyten, Alexandra M. Z. Slawin, Stuart J. Conway

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The synthesis of D-myo-inositol 1,4,5-trisphosphate (InsP(3)) from methyl alpha-D-glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP(3) derivatives. Biological evaluation of the synthetic InsP(3) demonstrates that this compound evokes selective Ca2+ release via activation of InsP(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)857-866
Number of pages10
JournalTetrahedron: Asymmetry
Volume20
Issue number6-8
Early online date1 Apr 2009
DOIs
Publication statusPublished - 7 May 2009

Keywords

  • Catalytic Asymmetric Phosphorylation
  • Pure Natural Inositols
  • Enantiomerically Pure
  • Adenophostin-A
  • Myoinositol 1,4,5-Trisphosphate
  • Penicillium-Brevicompactum
  • Trisphosphate Receptors
  • Expeditious Route
  • Potent Agonists
  • D-Galactose

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