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TitleDiscovery of C13-Aminobenzoyl Cycloheximide Derivatives that Potently Inhibit Translation Elongation.
Journal, issue, pagesJ Am Chem Soc, Vol. 143, Issue 34, Page 13473-13477, Year 2021
Publish dateSep 1, 2021
AuthorsYumi Koga / Eileen M Hoang / Yongho Park / Alexander F A Keszei / Jason Murray / Sichen Shao / Brian B Liau /
PubMed AbstractEmployed for over half a century to study protein synthesis, cycloheximide (CHX, ) is a small molecule natural product that reversibly inhibits translation elongation. More recently, CHX has been ...Employed for over half a century to study protein synthesis, cycloheximide (CHX, ) is a small molecule natural product that reversibly inhibits translation elongation. More recently, CHX has been applied to ribosome profiling, a method for mapping ribosome positions on mRNA genome-wide. Despite CHX's extensive use, CHX treatment often results in incomplete translation inhibition due to its rapid reversibility, prompting the need for improved reagents. Here, we report the concise synthesis of C13-amide-functionalized CHX derivatives with increased potencies toward protein synthesis inhibition. Cryogenic electron microscopy (cryo-EM) revealed that C13-aminobenzoyl CHX () occupies the same site as CHX, competing with the 3' end of E-site tRNA. We demonstrate that is superior to CHX for ribosome profiling experiments, enabling more effective capture of ribosome conformations through sustained stabilization of polysomes. Our studies identify powerful chemical reagents to study protein synthesis and reveal the molecular basis of their enhanced potency.
External linksJ Am Chem Soc / PubMed:34403584 / PubMed Central
MethodsEM (single particle)
Resolution3.2 - 4.1 Å
Structure data

23785

7mdz

EMDB-23785, PDB-7mdz:
80S rabbit ribosome stalled with benzamide-CHX
Method: EM (single particle) / Resolution: 3.2 Å

EMDB-23787:
80S rabbit ribosome stalled with CHX
Method: EM (single particle) / Resolution: 4.1 Å

Chemicals

ChemComp-MG:
Unknown entry

ChemComp-ZN:
Unknown entry

ChemComp-Z2V:
N-[(1R,3S,4R,5S)-3-{(1R)-2-[(2R,4r,6S)-2,6-dihydroxypiperidin-4-yl]-1-hydroxyethyl}-4-hydroxy-1,5-dimethylcyclohexyl]benzamide

Source
  • oryctolagus cuniculus (rabbit)
  • Rabbit (rabbit)
  • synthetic construct (others)
KeywordsRIBOSOME / 80S mammalian ribosome / translation inhibitor

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