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- Jul 29, 2018 · Traceless Staudinger Ligation 1.png 2,456 × 888; 30 KB Traceless Staudinger Ligation 2.png 2,629 × 539; 25 KB Traceless Staudinger Ligation 3.png 2,143 × 303; 19 KB 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.

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

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. 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) [61].

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.

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. 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 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 moiety as an intramolecular electrophilic trap. Martin Köckerling, Constantin Mamat, Structural and Kinetic Considerations for the Application of the Traceless Staudinger Ligation to Future 18F Radiolabeling Using XRD and 19F NMR, International Journal of Chemical Kinetics, 10.1002/kin.21137, 50, 1, (31-40), (2017). Site‐Selective Traceless Staudinger Ligation for Glycoprotein Synthesis Reveals Scope and Limitations Dr. Gonçalo J. L. Bernardes Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, OX1 3TA Oxford (UK), Fax: (+44) 1865‐285002