682-30-4Relevant articles and documents
Chemically Induced Vinylphosphonothiolate Electrophiles for Thiol-Thiol Bioconjugations
Baumann, Alice L.,Schwagerus, Sergej,Broi, Kevin,Kemnitz-Hassanin, Kristin,Stieger, Christian E.,Trieloff, Nils,Schmieder, Peter,Hackenberger, Christian P. R.
, p. 9544 - 9552 (2020)
Herein we introduce vinylphosphonothiolates as a new class of cysteine-selective electrophiles for protein labeling and the formation of stable protein-protein conjugates. We developed a straightforward synthetic route to convert nucleophilic thiols into electrophilic, thiol-selective vinylphosphonothiolates: In this protocol, intermediately formed disulfides can be chemoselectively substituted with vinylphosphonites under acidic conditions to yield the desired vinylphosphonothiolates. Notably, this reaction sequence enables the installation of vinylphosphonothiolate electrophiles directly on cysteine side chains within peptides and proteins. In addition to labeling the monoclonal antibody trastuzumab with excellent cysteine-selectivity, we applied our protocol for the site-specific conjugation of two proteins with unique cysteine residues yielding a nonhydrolyzable phosphonothiolate-linked diubiquitin and an ubiquitin-α-synuclein conjugate. The latter was recognized as a substrate in a subsequent enzymatic ubiquitination reaction.
Novel fluorinated dialkylphosphonatocholines: Synthesis, physicochemical properties and antiprotozoal activities against Acanthamoeba spp.
Luká?, Milo?,Garajová, Mária,Mrva, Martin,Devínsky, Ferdinand,Ondriska, Franti?ek,Kubincová, Janka
, p. 10 - 17 (2014/06/23)
The synthesis of four new organophosphorous gemini surfactants is presented. They belong to the class of dialkylphosphonatocholines. Tails are represented with two octyl groups both non or partially fluorinated. The synthesis was performed by reaction of alkylphosphonic acids with choline derivatives in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride. The micellar, surface active, and solubilization properties of new surfactants were studied. Antiprotozoal activities were tested against Acanthamoeba lugdunensis and Acanthamoeba quina.
Synthesis and characterization of novel tetrahedral copper(I) complexes comprising tridentate PNP-aminodiphosphines and tetradentate PN(X)P-substituted aminodiphosphines (X = O, S)
Peruzzo, Valentina,Pretzsch, Cornelia,Tisato, Francesco,Porchia, Marina,Refosco, Fiorenzo,Marzano, Cristina,Gandin, Valentina,Schiller, Eik,Walther, Martin,Pietzsch, Hans-Juergen
experimental part, p. 163 - 172 (2012/07/14)
Two series of novel tetrahedral copper(I) complexes comprising tridentate PNP-aminodiphosphines and tetradentate PN(X)P-substituted aminodiphosphines (X = O, S) have been prepared and characterized by conventional physico-chemical techniques. The first series includes '3 + 1'-type complexes comprising an aromatic PNP-aminodiphosphine and acetonitrile or triphenylphosphine. In the second series, the central amine function of the PNP-ligand was substituted with functionalized pendant arms containing ether, hydroxyl or thioether groups to enhance the chelation ability of the ligand. Fully coordinated neutral and cationic complexes were isolated. A preliminary study investigating both the labeling of 64Cu with the prototype PN(S)P ligand and the potential cytotoxic activity of the 'cold' [Cu(PN(S)P)][BF4] complex is reported.
