Total synthesis of a biotinylated rocaglate: Selective targeting of the translation factors eIF4AI/II

[Display omitted] 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...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2016-01, Vol.26 (2), p.262-264
Main Authors: Chambers, Jennifer M., Lindqvist, Lisa M., Savage, G. Paul, Rizzacasa, Mark A.
Format: Article
Language:English
Subjects:
Animals
Benzofurans - chemical synthesis
Benzofurans - chemistry
Benzofurans - pharmacology
Biotin - chemical synthesis
Biotin - chemistry
Biotin - pharmacology
Biotin tag
eIF4A
Eukaryotic Initiation Factor-4A - chemistry
Eukaryotic Initiation Factor-4A - metabolism
Methyl rocaglate
Mice
Pulldown
Rabbits
Silvestrol
Triterpenes - chemistry
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Summary:[Display omitted] 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).
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2015.12.045