Multigram synthesis of isobutyl-β- C -galactoside as a substitute of isopropylthiogalactoside for exogenous gene induction in mammalian cells

Lin Liu, Basma Abdel Motaal, Marc Schmidt-Supprian, Nicola L.B. Pohl

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

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.

Original languageEnglish
Pages (from-to)1539-1546
Number of pages8
JournalJournal of Organic Chemistry
Volume77
Issue number3
DOIs
StatePublished - 3 Feb 2012
Externally publishedYes

Fingerprint

Dive into the research topics of 'Multigram synthesis of isobutyl-β- C -galactoside as a substitute of isopropylthiogalactoside for exogenous gene induction in mammalian cells'. Together they form a unique fingerprint.

Cite this