title: Total synthesis of a biotinylated rocaglate: Selective targeting of the translation factors eIF4AI/II.
abstract: The total synthesis of a biotinylated derivative of methyl rocaglate is described. This compound was accessed from synthetic methyl rocaglate (2) via formation of the propargyl amide and subsequent click reaction with a biotin azide. Affinity purification revealed that biotinylated rocaglate (8) and methyl rocaglate (2) bind with high specificity to translation factors eIF4AI/II. This remarkable selectivity is in line with that found for the more complex rocaglate silvestrol (3).
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne, Melbourne, Victoria 3010, Australia.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Chambers
authors.affiliation: Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria 3052, Australia; Department of Medical Biology, The University of Melbourne, Parkville, Victoria 3010, Australia. Electronic address: lindqvist@wehi.edu.au.
authors.forename: Lisa M
authors.initials: LM
authors.lastname: Lindqvist
authors.affiliation: CSIRO Molecular and Health Technologies, Bayview Avenue, Victoria 3168, Australia.
authors.forename: G Paul
authors.initials: GP
authors.lastname: Savage
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne, Melbourne, Victoria 3010, Australia. Electronic address: masr@unimelb.edu.au.
authors.forename: Mark A
authors.initials: MA
authors.lastname: Rizzacasa
mesh_terms: D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001710:Biotin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D039601:Eukaryotic Initiation Factor-4A / Q000737:chemistry* / Q000378:metabolism; D051379:Mice; D011817:Rabbits; D014315:Triterpenes / Q000737:chemistry
chemical_list: D001572:Benzofurans; D014315:Triterpenes; C483989:methyl rocaglate; C489897:silvestrol; D001710:Biotin; D039601:Eukaryotic Initiation Factor-4A
keywords: Biotin tag; Methyl rocaglate; Pulldown; Silvestrol; eIF4A