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

Jan 03, 2013 · Staudinger ligation is then performed to generate the radiolabeled tracer by treating the phosphine ester with a radiolabeled azide having a PET radioisotope moiety. Inventors: Kasi, Dhanalakshmi (Los Angeles, CA, US) Gangadharmath, Umesh (Los Angeles, CA, US) Walsh, Joseph (Pacific Palisades, CA, US) Kolb, Hartmuth (Playa Del Rey, CA, US) of the Staudinger ligation is in the ligation of peptides at a variety of residues. Here, we demonstrate that the traceless Staudinger ligation can be achieved in water with a water-soluble reagent. Those reagents that provide a high yield of amide product discourage protonation of the nitrogen in the key iminophosphorane intermediate. 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. Reaction mechanism of Staudinger reaction and reduction Staudinger ligation. Of interest in chemical biology research, the Staudinger ligation is a modification of the classical Staudinger reaction in which an electrophilic trap (usually a methyl ester) is placed on the triaryl phosphine. [5] 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 Apr 23, 2013 · An efficient method has been developed for the salicylaldehyde ester-mediated ligation of unprotected peptides at serine (Ser) or threonine (Thr) residues. The utility of this peptide ligation approach has been demonstrated through the convergent syntheses of two therapeutic peptides––ovine-corticoliberin and Forteo––and the human erythrocyte acylphosphatase protein (∼11 kDa). Mar 12, 2013 · Staudinger ligation DOI: 10.1002/anie.201206533 Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides** Andrew D. Kosal, Erin E. Wilson, and Brandon L. Ashfeld* The synthesis of amide C N bonds through nucleophilic acyl substitutions constitutes one of the most fundamental trans-

of the Staudinger ligation is in the ligation of peptides at a variety of residues. Here, we demonstrate that the traceless Staudinger ligation can be achieved in water with a water-soluble reagent. Those reagents that provide a high yield of amide product discourage protonation of the nitrogen in the key iminophosphorane intermediate.

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 WARF reference number P00315US describes a method of using traceless Staudinger ligation for the total chemical synthesis of proteins. Publications Tam A., Soellner M.B. and Raines R.T. 2007. Water-Soluble Phosphinothiols for Traceless Staudinger Ligation and Integration with Expressed Protein Ligation. J. Am. Chem. Soc. 129, 11421–11430. BERKELEY, CA — No, the "Staudinger ligation" isn't the latest Robert Ludlum thriller; it's a new chemical reaction in a growing arsenal of cell engineering techniques developed by Carolyn Bertozzi of the Department of Energy's Lawrence Berkeley National Laboratory, a pioneer in modifying the surfaces of living cells.

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

Reaction Mechanism and Kinetics of the Traceless Staudinger Ligation. Journal of the American Chemical Society 2006, 128 (27) , 8820-8828. DOI: 10.1021/ja060484k. Aldo Bianchi and, Anna Bernardi. Traceless Staudinger Ligation of Glycosyl Azides with Triaryl Phosphines: Stereoselective Synthesis of Glycosyl Amides. 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 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 An approach combining traceless Staudinger ligation and protease‐catalyzed N‐terminal azidonation has been shown to be efficient for the convergent synthesis of glycopeptides without the cysteine limitation of native chemical ligation. 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 -NH 2 synthon.