Multigram Synthesis of
Isobutyl-β-<i>C</i>-galactoside as a Substitute of
Isopropylthiogalactoside for Exogenous
Gene Induction in Mammalian Cells
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Abstract
Herein we report that isobutyl-β-<i>C</i>-galactoside
(IBCG) is also a promising inducer of gene expression in mammalian
cells and report a new synthetic route to the compound that should
make obtaining the multigram quantities of material required for animal
studies more feasible. A convenient synthesis of IBCG, an inducer
of genes controlled by the <i>lac</i> operon system in bacterial
cells, was achieved in 5 steps from galactose in 81% overall yield
without any chromatographic separation steps. An optimized microwave-assisted
reaction at high concentration was key to making the <i>C-</i>glycosidic linkage. A Wittig reaction on a per<i>-O</i>-silylated rather than per-<i>O</i>-acetylated or -benzylated
substrate proved most effective in installing the final carbon atom