TY - JOUR
T1 - Preparation of azide biosynthetic surrogates of myo-inositol
AU - Pasari, Sandip
AU - Ismail, Shareef M.
AU - Wenk, Markus R.
AU - Lear, Martin J.
PY - 2015/1/23
Y1 - 2015/1/23
N2 - 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.
AB - 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.
KW - Biosynthesis
KW - Deoxy sugars
KW - Glycolipids
KW - Inositols
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KW - KTRSBMDLCXWFCL-QWBQGLJISA-N
KW - KTRSBMDLCXWFCL-UOTPTPDRSA-N
KW - KTRSBMDLCXWFCL-XCMZKKERSA-N
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U2 - 10.1016/j.tetlet.2015.04.009
DO - 10.1016/j.tetlet.2015.04.009
M3 - Article
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
ER -