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

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 Apr 07, 2008 · Putative mechanism of the traceless Staudinger ligation. Recently, we reported a new reagent, di(4-methoxyphenyl)phosphinomethanethiol ( 2 ), that is effective at mediating ligations between encumbered residues. 12 Results indicated that electron-donating substituents on the aryl rings disfavor the formation of a side product, thereby leading

Site-Selective Traceless Staudinger Ligation for Glycoprotein Synthesis Reveals Scope and Limitations GonÅalo J. L. Bernardes, Lars Linderoth, Katie J. Doores, Omar Boutureira, and Benjamin G. Davis*[a] Efficient, chemoselective reactions enable access to well-de-fined post-translationally modified proteins.[1–4] One approach

Jan 01, 2009 · The traceless Staudinger ligation has joined the repertoire of ligation methods for the convergent synthesis of proteins. This method has been used along with others to assemble an entire protein. A putative strategy for the assembly of proteins is depicted in Fig. 4 ( Nilsson et al. , 2003b ). Inspired by the traceless Staudinger ligation reaction developed by Bertozzi, Raines, and coworkers for the conversion of an azide to an acyl amide, [9, 10] we perceived that the genetic Site-Selective Traceless Staudinger Ligation for Glycoprotein Synthesis Reveals Scope and Limitations GonÅalo J. L. Bernardes, Lars Linderoth, Katie J. Doores, Omar Boutureira, and Benjamin G. Davis*[a] Efficient, chemoselective reactions enable access to well-de-fined post-translationally modified proteins.[1–4] One approach

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

a cysteine residue at the ligation junction.1 The Staudinger ligation is one such strategy.7,8 In one version of the Staudinger ligation, a peptide with a C-terminal phosphinothioester is coupled with a second peptide having an N-terminal azido acid to form a new peptide bond in a traceless manner, without The Staudinger-Bertozzi ligation [1]: 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.