title: Multigram synthesis of isobutyl-β-C-galactoside as a substitute of isopropylthiogalactoside for exogenous gene induction in mammalian cells.
abstract: 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.
authors.affiliation: Department of Chemistry, Plant Sciences Institute, Hach Hall, Iowa State University, Ames, Iowa 50011-3111, USA.
authors.forename: Lin
authors.initials: L
authors.lastname: Liu
authors.forename: Basma
authors.initials: B
authors.lastname: Abdel Motaal
authors.forename: Marc
authors.initials: M
authors.lastname: Schmidt-Supprian
authors.forename: Nicola L B
authors.initials: NL
authors.lastname: Pohl
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005818:Genetic Engineering; D006367:HeLa Cells; D006801:Humans; D007544:Isopropyl Thiogalactoside / Q000494:pharmacology*; D015533:Transcriptional Activation / Q000187:drug effects*
chemical_list: D005697:Galactosides; C476523:isobutyl-C-galactoside; D007544:Isopropyl Thiogalactoside