Abstract
The synthesis of D-myo-inositol 1,4,5-trisphosphate (InsP(3)) from methyl alpha-D-glucopyranose, via a type 2 Ferrier rearrangement is reported. A key intermediate in this synthesis possesses orthogonal protecting groups at the 1-, 4- and 5-position, making it a versatile starting point for the synthesis of unnatural InsP(3) derivatives. Biological evaluation of the synthetic InsP(3) demonstrates that this compound evokes selective Ca2+ release via activation of InsP(3) receptors. (C) 2009 Elsevier Ltd. All rights reserved.
Original language | English |
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Pages (from-to) | 857-866 |
Number of pages | 10 |
Journal | Tetrahedron: Asymmetry |
Volume | 20 |
Issue number | 6-8 |
Early online date | 1 Apr 2009 |
DOIs | |
Publication status | Published - 7 May 2009 |
Keywords
- Catalytic Asymmetric Phosphorylation
- Pure Natural Inositols
- Enantiomerically Pure
- Adenophostin-A
- Myoinositol 1,4,5-Trisphosphate
- Penicillium-Brevicompactum
- Trisphosphate Receptors
- Expeditious Route
- Potent Agonists
- D-Galactose