30247-98-4Relevant articles and documents
Ionic reagent for controlling the gas-phase fragmentation reactions of cross-linked peptides
Lu, Yali,Tanasova, Marina,Borhan, Babak,Reid, Gavin E.
, p. 9279 - 9287 (2008)
Chemical cross-linking combined with proteolytic digestion and mass spectrometry (MS) is a promising approach to provide inter- and intramolecular distance constraints for the structural characterization of protein topologies and functional multiprotein complexes. Despite the relative straightforwardness of these methodologies, the identification and characterization of cross-linked proteins presents a significant analytical challenge, due to the complexity of the resultant peptide mixtures, as well as the array of inter-, intra-, or dead-end -cross-linked peptides that may be generated from a single cross-linking experiment. To address these issues, we describe here the synthesis, characterization, and initial evaluation of a novel fixed charge sulfonium ion-containing cross-linking reagent, S-methyl 5,5′-thiodipentanoylhydroxysuccinimide. The peptide products obtained by reaction with this reagent are all shown to fragment exclusively via facile cleavage of the C-S bond directiy adjacent to the fixed charge during CID-MS/MS, resulting in the formation of characteristic product ions that enable the presence and type (i.e., inter, intra, or dead-end) of the cross-linked products to be readily determined, independently of the proton mobility of the precursor ion. Subsequent isolation and dissociation of these products by MS3 provides additional structural information required for identification of the peptide sequences involved in the cross-linking reactions, as well as for characterization of the specific site(s) at which cross-linking has occurred. The specificity of these gas-phase fragmentation reactions, as well as the solubility and stability of the cross-linking reagent under aqueous conditions, suggests that this strategy holds great promise for use in future studies aimed at the structural analysis of large proteins or multiprotein assemblies.
Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes
McCourt, Ruairí O.,Scanlan, Eoin M.
supporting information, p. 15804 - 15810 (2020/10/26)
A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.
Modular Bidentate Hybrid NHC-Thioether Ligands for the Stabilization of Palladium Nanoparticles in Various Solvents
Rühling, Andreas,Schaepe, Kira,Rakers, Lena,Vonh?ren, Benjamin,Tegeder, Patricia,Ravoo, Bart Jan,Glorius, Frank
supporting information, p. 5856 - 5860 (2016/05/09)
The synthesis of four different bidentate hybrid NHC-thioether ligands is presented. The corresponding palladium nanoparticles are stable in various solvents, depending on the ligand used, and show high chemoselectivity in the hydrogenation of olefins. The solubility of the nanoparticles can be switched multiple times depending on the pH value of the solvent. XPS analysis (which shows a subtle shift in the binding energy) was identified as a convenient tool to establish the binding mode of NHC ligands.
99mTc labeled myocardial imaging agents of long-chain fatty acid: An intermediate synthesis process research
Huo, Qing,Xue, Jingquan,Liu, Yu
, p. 8621 - 8624 (2013/11/06)
Myocardial fatty acid metabolic imaging agent can be used for studying the myocardial ischemia positioning, measurements reflect changes in myocardial metabolic function and the detection of myocardial cell survival, provide a reliable basis for the clinical diagnosis of cardiac disease. In this paper, we study the synthesis of fatty brominated products BSE, which is the intermediates of novel 99mTclabeled fatty acid metabolic imaging agent. The final yield of the product was 38 %, NMR spectroscopy confirmed very consistent the hydrogen peak displacement and integral spectrum area with the goal of formula. This synthetic route is convenient, simple, economic and has a potential value of industrial applications.
