1355357-75-3Relevant academic research and scientific papers
Multigram synthesis of isobutyl-β- C -galactoside as a substitute of isopropylthiogalactoside for exogenous gene induction in mammalian cells
Liu, Lin,Abdel Motaal, Basma,Schmidt-Supprian, Marc,Pohl, Nicola L. B.
, p. 1539 - 1546 (2012/04/04)
Herein we report that isobutyl-β-C-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 lac 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 C-glycosidic linkage. A Wittig reaction on a per-O-silylated rather than per-O-acetylated or -benzylated substrate proved most effective in installing the final carbon atom.
