Title: Regioselective deprotection of orthobenzoates for the synthesis of inositol phosphates
Authors: Swarbrick, Joanna
Cooper, Samuel
Bultynck, Geert ×
Gaffney, Piers #
Issue Date: 21-Apr-2009
Publisher: Royal Society of Chemistry
Series Title: Organic & Biomolecular Chemistry vol:7 issue:8 pages:1709-1715
Abstract: Synthetic myo-inositol 1,4,5-triphosphate, Ins(1,4,5)P3, and myo-inositol 1,3,4,5-tetraphosphate, Ins(1,3,4,5)P4, continue to be valuable in biological studies. Inositol orthoesters have proved an important class of intermediate to access these compounds. We investigated the ability of steric bulk from a 4-O protecting group to direct DIBAL-H reduction of inositol orthobenzoates to generate the natural Ins(1,4,5)P3 precursor 2,3,6-O-tribenzyl myo-inositol. Introduction of an equatorial 4-C-methyl group imparts totally selective reduction and we report the synthesis of novel 4-C-methyl-Ins(1,4,5)P3 and 4-C-methyl-Ins(1,3,4,5)P4.
Description: * Acids/chemistry
* Animals
* Benzoates/chemical synthesis*
* Benzoates/chemistry
* Calcium/metabolism
* Cell Line
* Hydrolysis
* Inositol 1,4,5-Trisphosphate/chemical synthesis*
* Inositol 1,4,5-Trisphosphate/metabolism
* Inositol Phosphates/chemical synthesis*
* Oxidation-Reduction
* Stereoisomerism
ISSN: 1477-0520
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Molecular and Cellular Signaling
× corresponding author
# (joint) last author

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