Thienyl-Substituted α-Ketoamide: A Less Hydrophobic Reactive Group for Photo-Affinity Labeling

Eisuke Ota, Kazuteru Usui, Kana Oonuma, Hiroyuki Koshino, Shigeru Nishiyama, Go Hirai, Mikiko Sodeoka

Research output: Contribution to journalArticle

3 Citations (Scopus)

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 languageEnglish
Pages (from-to)876-880
Number of pages5
JournalACS Chemical Biology
Volume13
Issue number4
DOIs
Publication statusPublished - Apr 20 2018

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Mannose
Labeling
Photolysis
Concanavalin A
Hydrophobic and Hydrophilic Interactions
Research
Photodegradation
Hydrophobicity
Proteins
Substitution reactions

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 journalArticle

Ota, Eisuke ; Usui, Kazuteru ; Oonuma, Kana ; Koshino, Hiroyuki ; Nishiyama, Shigeru ; Hirai, Go ; Sodeoka, Mikiko. / Thienyl-Substituted α-Ketoamide : A Less Hydrophobic Reactive Group for Photo-Affinity Labeling. In: ACS Chemical Biology. 2018 ; Vol. 13, No. 4. pp. 876-880.
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