Preparation of azide biosynthetic surrogates of myo-Inositol

Pasari, Sandip, Ismail, Shareef M., Wenk, Markus R. and Lear, Martin (2015) Preparation of azide biosynthetic surrogates of myo-Inositol. Tetrahedron Letters, 56 (20). pp. 2597-2601. ISSN 0040-4039

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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.

Keywords:Inositol, Deoxy sugars, Glycolipids, Biosynthesis, JCNotOpen
Subjects:F Physical Sciences > F165 Biomolecular Chemistry
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F163 Bio-organic Chemistry
Divisions:College of Science > School of Chemistry
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ID Code:17094
Deposited On:14 Apr 2015 19:57

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