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Synthesis and Biological Evaluation of 1,5-Dideoxy-1,5-iminoxylitol-Amino Acid Hybrids as Xylosidase Inhibitors

TitleSynthesis and Biological Evaluation of 1,5-Dideoxy-1,5-iminoxylitol-Amino Acid Hybrids as Xylosidase Inhibitors
Publication TypeJournal Article
Year of Publication2009
AuthorsSteiner, AJ, Stuetz, AE, Tarling, CA, Withers, SG, Wrodnigg, TM
JournalAUSTRALIAN JOURNAL OF CHEMISTRY
Volume62
Pagination553-557
ISSN0004-9425
Abstract

1,5-Dideoxy-1,5-iminoxylitol-amino acid hybrids have been synthesized by cyclisation via a double reductive amination of xylo-pentodialdose and the respective amino groups of lysine as well as serine components. Further modification with aromatic substituents gave access to lipophilic derivatives. Kinetic studies revealed that all compounds exhibited better inhibitory properties against beta-xylosidase from Thermoanaerobacterium sacharolyticum than the parent iminosugar.

DOI10.1071/CH09040