Journal article
Total synthesis of a biotinylated rocaglate: Selective targeting of the translation factors eIF4AI/II
JM Chambers, LM Lindqvist, GP Savage, MA Rizzacasa
Bioorganic and Medicinal Chemistry Letters | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2016
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).
Grants
Awarded by National Health and Medical Research Council
Funding Acknowledgements
We thank the Australian Research Council-Discovery Grants Scheme for funding. LML holds an NHMRC Peter Doherty Early Career Fellowship (1035502). Research on this subject is supported by the Victorian State Government Operational Infrastructure Support and Australian Government NHMRC IRIISS to WEHI (LML).