Intracellular Mediators: Synthesis of l-α-Phosphatidyl-d-myo-inositol 3,4,5-Trisphosphate and Glyceryl Ether Analogs

K. Kishta Reddy, Mourad Saady, J R Falck, Gregg Whited

Research output: Contribution to journalArticle

70 Scopus citations

Abstract

L-α-Phosphatidyl-d-myo-inositol 3,4,5-trisphosphate (3,4,5-PIP3), the most prominent member of a new class of intracellular second messengers, and two ether analogs were conveniently prepared from the differentially functionalized d-myo-inositol intermediate 7 which was ultimately derived from the unique cyclitol precursor dehydroshikimic acid (1). Critical transformations included the stereoselective hydride reduction of the shikimate ketone, exclusive osmylation from the α-face to give 3, controlled enolization of 4, and dioxirane epoxidation with in situ rearrangement affording ketone 5. Dioctanoyl 3,4,5-PIP3 (9a) and its dioctyl ether analog 9b selectively activated the δ, ∈, and η-isotypes of protein kinase C (PKC).

Original languageEnglish (US)
Pages (from-to)3385-3390
Number of pages6
JournalJournal of Organic Chemistry
Volume60
Issue number11
DOIs
StatePublished - Jun 1 1995

ASJC Scopus subject areas

  • Organic Chemistry

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