The Staudinger-Bertozzi ligation : Bertozzi developed the Staudinger-then-aza-Wittig reaction shown below and demonstrated its utility in ligating large phosphorescent compounds by the amide bond. This reaction is high yielding and highly chemoselective, offering possibilities for applications in various chemical biology researches.
Traceless Staudinger ligation: Traceless Staudinger ligation was developed by Bertozzi based on the Staudinger reaction. The ligation performs between C-terminal thioester-phosphine and N-terminal azide to form an iminophosphorane intermediate followed by aza-ylide-thioester transfer to form a native amide bond (Figure 1G) . Dec 25, 2014 · An azidonorleucine residue is installed at a desired site in a substrate protein by nonnatural amino acid incorporation, and a phosphinothioester is installed at the C terminus of a pendant protein by expressed protein ligation. Then, the traceless Staudinger ligation is used to link the substrate and pendant proteins via an isopeptide bond. Reaction mechanism and kinetics of the traceless Staudinger ligation MB Soellner, BL Nilsson, RT Raines Journal of the American Chemical Society 128 (27), 8820-8828 , 2006 Dec 05, 2014 · The DNA ligation reaction itself has two basic steps. Firstly the DNA ends have to collide by chance and stay together long enough for the ligase to join them. This is the most inefficient part of the reaction, but is easier at low temperatures.
May 23, 2006 · This supports a 'ground-state destabilization' reaction mechanism for the first cleavage step in protein splicing. E., Armstrong, J.I. & Bertozzi, C.R.A. “Traceless” Staudinger ligation
Keywords:Self-assembled monolayers (SAM), traceless staudinger ligation, biotinylation, surface modification, thiol-gold attachment, surface characterization. Abstract:Background: Formation of Self-assembled monolayers (SAMs) is one of the most widely used methods to modify a surface to achieve the desired property. It is a very unique, yet
The so-called traceless Staudinger ligation is a highly attractive process leading to a native amide bond without inclusion of the phosphine oxide in the final product. 6 The synthetic value of this remarkable transformation has been demonstrated by Raines and coworkers with the ligation of complex peptide fragments, possibly best illustrated
Jul 12, 2006 · 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. A detailed mechanism of the traceless Staudinger ligation is depicted in Scheme 2. In this mechanism, phosphinothioester 19 and azide 20 react to form phosphazide 21 (Step 1), which gives iminophosphorane 22 with concomitant release of N 2 (g) (Step 2). Abstract. Abstract The traceless Staudinger ligation of azides and phosphines is an effective method to produce an amide bond. In this work, density functional theory (DFT) calculations were carried out to investigate the mechanism of the traceless Staudinger ligation, which suggested that its rate-limiting step was the attack of azide on phosphine leading to the formation of phosphazide. Keywords:Self-assembled monolayers (SAM), traceless staudinger ligation, biotinylation, surface modification, thiol-gold attachment, surface characterization. Abstract:Background: Formation of Self-assembled monolayers (SAMs) is one of the most widely used methods to modify a surface to achieve the desired property. It is a very unique, yet Direct Acyl Substitution of Carboxylic Acids: A Chemoselective O‐ to N‐Acyl Migration in the Traceless Staudinger Ligation Andrew D. Kosal Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556 (USA), Fax: (+1) 574‐631‐6652