Preparation of azide biosynthetic surrogates of myo-inositol

Sandip Pasari, Shareef M. Ismail, Markus R. Wenk, Martin J. Lear

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

As a prelude to biomolecular incorporation studies, practical routes to a series of four regioisomeric azido-deoxy derivatives of inositol that mimic the natural myo-stereochemistry are described. Starting from commercially available myo-inositol, the regioselective and stereoselective introduction of azide functionality was achieved at the C-2, C-3, C-4, and C-5 positions via azide displacement of the corresponding O-sulfonates of suitably protected scyllo-, chiro-, epi-, and neo-inositols, respectively. Notably, a final one-pot acetolysis method conveniently allowed for rapid access to pentaacetate azido-deoxy inositols. Investigations on the metabolic incorporation of these myo-inositol azide surrogates in both acetate and free alcohol forms are in progress.

Original languageEnglish
JournalTetrahedron Letters
DOIs
Publication statusAccepted/In press - 2015 Jan 23

Keywords

  • Biosynthesis
  • Deoxy sugars
  • Glycolipids
  • Inositols
  • KTRSBMDLCXWFCL-KXXVROSKSA-N
  • KTRSBMDLCXWFCL-QWBQGLJISA-N
  • KTRSBMDLCXWFCL-UOTPTPDRSA-N
  • KTRSBMDLCXWFCL-XCMZKKERSA-N

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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