Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 26, Issue 2, Pages 262-264Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2015.12.045
Keywords
Methyl rocaglate; Silvestrol; Biotin tag; eIF4A; Pulldown
Categories
Funding
- Australian Research Council
- NHMRC [1035502]
- Victorian State Government Operational Infrastructure Support
- Australian Government NHMRC IRIISS
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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). (C) 2015 Elsevier Ltd. All rights reserved.
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