Preparation of azide biosynthetic surrogates of myo-inositol

TETRAHEDRON LETTERS

卷:56

Article

Pasari, Sandip^1,2  Ismail, Shareef M.³  Wenk, Markus R.^3,4,5  Lear, Martin J.^1,2,6 

[1] Natl Univ Singapore, Fac Sci, Dept Chem, Singapore 117543, Singapore

[2] Natl Univ Singapore, Fac Sci, Med Chem Program, Singapore 117543, Singapore

[3] Natl Univ Singapore NUS, Grad Sch Integrat Sci & Engn NGS, Ctr Life Sci, Singapore 117456, Singapore

[4] Natl Univ Singapore, Yong Loo Sch Med, Dept Biochem, Singapore 117543, Singapore

[5] Natl Univ Singapore, Yong Loo Sch Med, Dept Biol Sci, Singapore 117543, Singapore

[6] Lincoln Univ, Sch Chem, Lincoln LN6 7TS, Lincs, England

关键词: Inositols;    Deoxy sugars;    Biosynthesis;    Glycolipids;   

DOI  :  10.1016/j.tetlet.2015.04.009

来源: Elsevier

【 摘 要 】

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. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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