818-68-8Relevant articles and documents
Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes
Am Ende, Christopher W.,Asare-Okai, Papa Nii,Fox, Joseph M.,Jemas, Andrew,O'brien, Jessica G. K.
, p. 9415 - 9420 (2020)
Dialkyldiazirines have emerged as reagents of choice for biological photoaffinity labeling studies. The mechanism of crosslinking has dramatic consequences for biological applications where instantaneous labeling is desirable, as carbene insertions display different chemoselectivity and are much faster than competing mechanisms involving diazo or ylide intermediates. Here, deuterium labeling and diazo compound trapping experiments are employed to demonstrate that both carbene and diazo mechanisms operate in the reactions of a dialkyldiazirine motif that is commonly utilized for biological applications. For the fraction of intermolecular labeling that does involve a carbene mechanism, direct insertion is not necessarily involved, as products derived from a carbonyl ylide are also observed. We demonstrate that a strained cycloalkyne can intercept diazo compound intermediates and serve as a bioorthogonal probe for studying the contribution of the diazonium mechanism of photoaffinity labeling on a model protein under aqueous conditions.
Ionic-liquid-catalyzed efficient transformation of γ-valerolactone to methyl 3-pentenoate under mild conditions
Zeng, Fan-Xin,Liu, Hai-Feng,Deng, Li,Liao, Bing,Pang, Hao,Guo, Qing-Xiang
, p. 600 - 603 (2013/07/27)
Green nylons! Acidic ionic-liquid catalysis for the transformation of g-valerolactone into methyl 3-pentenoate (M3P) is shown to be performed efficiently under mild conditions. M3P is obtained selectively from a reaction at 1708C for 3.5 h in the presence of an acidic ionic liquid that has a low vapor pressure, high thermal stability, and excellent catalytic performance. A possible reaction pathway for this conversion is also presented.