Jun 24, 2011
Jun 24, 2011 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 The Staudinger Ligation | Chemical Reviews While the Staudinger reaction has first been described a hundred years ago in 1919, the ligation reaction became one of the most important and efficient bioconjugation techniques in the 1990s and this century. It holds the crucial characteristics for bioorthogonal chemistry: biocompatibility, selectivity, and a rapid and high-yielding turnover for a wide variety of applications. In the past Staudinger Reaction - Organic Chemistry Staudinger Reaction Staudinger Reduction. Azides may be converted to amines by hydrogenation, but another possibility is the Staudinger Reaction, which is a very mild azide reduction. As there are a variety of methods for preparing azides readily, the Staudinger Reaction makes it possible to use -N 3 as an …
Convergent Glycopeptide Synthesis by Traceless Staudinger
The traceless Staudinger ligation can be mediated in water without organic co-solvents if charged groups render the phenylphosphine reagent water soluble. Here the synthesis of a new water-soluble phosphine is presented based on a diphenylphosphinophenol reagent. Staudinger ligation with this reagent and azido glycine amide showed UvA-DARE (Digital Academic Repository) Enzymatic tools for
Electronic and Steric Effects on the Rate of the Traceless
Synthesis of Water-Soluble Phosphinophenol for Traceless the Ligation reaction an intramolecular acetylation of the iminophosphorane takes place, and after hydrolysis an amide bond is formed.5 In the traceless variant the arylphosphine is part of the leaving group, and just a na tive amide bond between the ligation partners is formed (Scheme 1).6 Thus the traceless Staudinger ligation is es Reaction Mechanism and Kinetics of the Traceless