25055-86-1Relevant articles and documents
Improved synthesis of photo-leucine
Ikeda, Yoshio,Behrman
, p. 2276 - 2284 (2008)
An improved and reproducible synthesis of photo-leucine [3-(3-methyl-3-diazirinyl)-alanine] is presented. Copyright Taylor & Francis Group, LLC.
Diazirine-containing photoactivatable isoprenoid: Synthesis and application in studies with isoprenylcysteine carboxyl methyltransferase
Vervacke, Jeffrey S.,Funk, Amy L.,Wang, Yen-Chih,Strom, Mark,Hrycyna, Christine A.,Distefano, Mark D.
, p. 1971 - 1978 (2014)
Photoaffinity labeling is a useful technique employed to identify protein-ligand and protein-protein noncovalent interactions. Photolabeling experiments have been particularly informative for probing membrane-bound proteins where structural information is difficult to obtain. The most widely used classes of photoactive functionalities include aryl azides, diazocarbonyls, diazirines, and benzophenones. Diazirines are intrinsically smaller than benzophenones and generate carbenes upon photolysis that react with a broader range of amino acid side chains compared with the benzophenone-derived diradical; this makes diazirines potentially more general photoaffinity-labeling agents. In this article, we describe the development and application of a new isoprenoid analogue containing a diazirine moiety that was prepared in six steps and incorporated into an a-factor-derived peptide produced via solid-phase synthesis. In addition to the diazirine moiety, fluorescein and biotin groups were also incorporated into the peptide to aid in the detection and enrichment of photo-cross-linked products. This multifuctional diazirine-containing peptide was a substrate for Ste14p, the yeast homologue of the potential anticancer target Icmt, with Km (6.6 μM) and Vmax (947 pmol min-1 mg-1) values comparable or better than a-factor peptides functionalized with benzophenone-based isoprenoids. Photo-cross-linking experiments demonstrated that the diazirine probe photo-cross-linked to Ste14p with observably higher efficiency than benzophenone-containing a-factor peptides.
One-Pot Synthesis of Diazirines and 15N2-Diazirines from Ketones, Aldehydes and Derivatives: Development and Mechanistic Insight
Ibert, Quentin,Cauwel, Madeleine,Glachet, Thomas,Tite, Tony,Le Nahenec-Martel, Patricia,Lohier, Jean-Fran?ois,Renard, Pierre-Yves,Franck, Xavier,Reboul, Vincent,Sabot, Cyrille
supporting information, p. 4390 - 4398 (2021/08/03)
Broad scope one-pot diazirine synthesis strategies have been developed using two different oxidants depending on the nature of the starting material. In all cases, an inexpensive commercial solution of ammonia (NH3) in methanol (MeOH) was emplo
PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS
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Page/Page column 73; 75-77, (2021/04/01)
Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.
