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.
| Original language | English |
|---|---|
| Pages (from-to) | 876-880 |
| Number of pages | 5 |
| Journal | ACS Chemical Biology |
| Volume | 13 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2018 Apr 20 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
Cite this
Thienyl-Substituted α-Ketoamide : A Less Hydrophobic Reactive Group for Photo-Affinity Labeling. / Ota, Eisuke; Usui, Kazuteru; Oonuma, Kana; Koshino, Hiroyuki; Nishiyama, Shigeru; Hirai, Go; Sodeoka, Mikiko.
In: ACS Chemical Biology, Vol. 13, No. 4, 20.04.2018, p. 876-880.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Thienyl-Substituted α-Ketoamide
T2 - A Less Hydrophobic Reactive Group for Photo-Affinity Labeling
AU - Ota, Eisuke
AU - Usui, Kazuteru
AU - Oonuma, Kana
AU - Koshino, Hiroyuki
AU - Nishiyama, Shigeru
AU - Hirai, Go
AU - Sodeoka, Mikiko
PY - 2018/4/20
Y1 - 2018/4/20
N2 - 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.
AB - 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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U2 - 10.1021/acschembio.7b00988
DO - 10.1021/acschembio.7b00988
M3 - Article
VL - 13
SP - 876
EP - 880
JO - ACS Chemical Biology
JF - ACS Chemical Biology
SN - 1554-8929
IS - 4
ER -