AI Article Synopsis
- Photoaffinity labeling (PAL) is limited by the photoinstability of α-ketoamides, but 2-thienyl-substituted α-ketoamides offer a more effective solution for this technique.
- The introduction of 2-thienyl substitution decreases the electrophilicity of the keto group and slows down photodegradation, leading to improved stability.
- Mannose-conjugated thienyl α-ketoamides demonstrate enhanced labeling efficiency for concanavalin A and show less labeling of nontarget proteins due to their lower hydrophobicity compared to other conventional photoreactive groups.
Article Abstract
Photoaffinity labeling (PAL) is an important tool in chemical biology research, but application of α-ketoamides for PAL has been hampered by their photoinstability. Here, we show that 2-thienyl-substituted α-ketoamide is a superior photoreactive group for PAL. Studies with a series of synthetic mannose-conjugated α-ketoamides revealed that 2-thienyl substitution of α-ketoamide decreased the electrophilicity of the keto group and reduced the rate of photodegradation. Mannose-conjugated thienyl α-ketoamide showed greater concanavalin A labeling efficiency than other alkyl or phenyl-substituted α-ketoamides. In comparison with representative conventional photoreactive groups, 2-thienyl ketoamide showed reduced labeling of nontarget proteins, probably owing to its lower hydrophobicity.
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| http://dx.doi.org/10.1021/acschembio.7b00988 | DOI Listing |
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