Thienyl-Substituted α-Ketoamide: A Less Hydrophobic Reactive Group for Photo-Affinity Labeling,ACS Chemical Biology

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Thienyl-Substituted α-Ketoamide: A Less Hydrophobic Reactive Group for Photo-Affinity Labeling
ACS Chemical Biology ( IF 3.5 ) Pub Date : 2018-02-19 00:00:00 , DOI: 10.1021/acschembio.7b00988
Eisuke Ota _{1,

2} , Kazuteru Usui ₃ , Kana Oonuma ₄ , Hiroyuki Koshino ₄ , Shigeru Nishiyama ₂ , Go Hirai _{1,

3,

4} , Mikiko Sodeoka _{1,

4,

5}

Affiliation

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.

中文翻译：

噻吩基取代的α-酮酰胺：较少的疏水性反应基团，用于光亲和标记

光亲和标记（PAL）是化学生物学研究中的重要工具，但是α-酮酰胺在PAL中的应用由于其光不稳定性而受到阻碍。在这里，我们表明2-噻吩基取代的α-酮酰胺是PAL的优良光反应性基团。对一系列合成甘露糖缀合的α-酮酰胺的研究表明，α-酮酰胺的2-噻吩基取代会降低酮基的亲电性，并降低光降解速率。甘露糖缀合的噻吩基α-酮酰胺比其他烷基或苯基取代的α-酮酰胺显示更高的伴刀豆球蛋白A标记效率。与代表性的常规光反应性基团相比，2-噻吩基酮酰胺的非靶蛋白标记减少，可能是由于其较低的疏水性。

更新日期：2018-02-19

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