Preparation of azide biosynthetic surrogates of myo-inositol

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

研究成果: Article査読

4 被引用数 (Scopus)

抄録

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.

本文言語English
ジャーナルTetrahedron Letters
DOI
出版ステータスAccepted/In press - 2015 1 23

ASJC Scopus subject areas

  • 生化学
  • 有機化学
  • 創薬

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