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Identification of Small Molecule-binding Proteins in a Native Cellular Environment by Live-cell Photoaffinity Labeling
Published on: September 20, 2016
Fluorous aryldiazirine photoaffinity labeling reagents.
1Division of Medicinal Chemistry and Natural Products, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
Organic Letters
|October 8, 2009
Summary
New fluorous photoaffinity labeling reagents were synthesized. These reagents offer efficient separation on fluorous silica gel and mild coupling capabilities for various molecules.
Area of Science:
- Organic Chemistry
- Chemical Biology
Background:
- Photoaffinity labeling (PAL) is a powerful technique for studying molecular interactions.
- Trifluoromethyldiazirines are effective photo-reactive groups for PAL.
- Incorporating fluorous tags can aid in the purification of reaction products.
Purpose of the Study:
- To design and synthesize novel fluorous derivatives of trifluoromethyldiazirine.
- To evaluate the reactivity and utility of these new reagents in photoaffinity labeling.
- To enable efficient purification and conjugation of the labeling reagents.
Main Methods:
- Synthesis of two fluorous trifluoromethyldiazirine derivatives.
- Activation of reagents in methanol and assessment of reactivity.
- Purification of reaction products using fluorous silica gel.
- Conversion of alcohol groups to activated carboxylic acid and amine functionalities.
Main Results:
- Successful synthesis of two fluorous trifluoromethyldiazirine derivatives.
- Reactivity comparable to the parent aryltrifluoromethyldiazirine when activated in methanol.
- Efficient separation of reaction products over fluorous silica gel.
- Demonstrated mild conditions for coupling with small molecules and macromolecules via activated functional groups.
Conclusions:
- The developed fluorous trifluoromethyldiazirine reagents are effective tools for photoaffinity labeling.
- Their fluorous nature facilitates simplified purification of labeling products.
- The versatile functional groups allow for broad applicability in labeling diverse biomolecules.
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