Staudinger ligation towards cyclodextrin dimers in aqueous

Reaction Mechanism and Kinetics of the Traceless The traceless Staudinger ligation enables the formation of an amide bond between a phosphinothioester (or phosphinoester) and an azide without the incorporation of residual atoms. Here, the coupling of peptides by this reaction was characterized in detail. Experiments with [18O]H2O indicated that the reaction mediated by (diphenylphosphino)methanethiol proceeded by S→N acyl transfer of the Nontraceless Staudinger Ligation | Sigma-Aldrich Nontraceless Staudinger Ligation. By: Matthias Junkers, Aldrich ChemFiles 2008, 8.1, 7. Aldrich ChemFiles 2008, 8.1, 7. Bertozzi et al. pioneered the application of the Staudinger reaction as a ligation method for bioconjugates. In the course of their studies on the metabolic engineering of cell surfaces they designed a phosphine with an ester Synthesis, structure determination, and (radio Jun 24, 2011

The Staudinger ligation of phosphine-substituted thioesters with 18 F-fluoroethylazide has been successfully applied to access 18 F-labelled molecules in radiochemical yields superior to 95%; the first fluorous variant of a Staudinger radio-ligation has been validated.

Other Staudinger ligation induced macrocyclizations have been published previously by Maarseveen and co-workers, who successfully used the Raines ligation reagent for the synthesis of a series of medium-sized lactams. 4 Wong and co-workers reported the synthesis of 14 different glycopeptides through the traceless Staudinger Ligation. 5 For this work, they also developed a protease-catalyzed A “Traceless” Staudinger Ligation for the Chemoselective

The traceless Staudinger ligation enables the formation of an amide bond between a phosphinothioester (or phosphinoester) and an azide without the incorporation of residual atoms. Here, the coupling of peptides by this reaction was characterized in detail. Experiments with [(18)O]H(2)O indicated that the reaction mediated by (diphenylphosphino)methanethiol proceeded by S-->N acyl transfer of

Traceless Staudinger Ligation. Emerging strategies for the unconstrained engineering of proteins avoid the requisite cysteine residues (Nilsson et al., 2005).Here, we describe one such strategy—the Staudinger ligation, which is based on the Staudinger reaction (Staudinger & Meyer, 1919).In the Staudinger reaction, a phosphine is used to reduce an azide to an amine: PR 3 + N 3 R′ + H 2 O A Photo‐Triggered Traceless Staudinger–Bertozzi Ligation Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2 ) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo‐induced heterolytic bond‐cleavage at the optimal wavelength