Project Methods The approach is to use ribonuclease A, the best characterized ribonuclease, as atemplate for the construction of hybrid proteins. Because RNase A lacks cytotoxic activity, any such activity in a hybrid protein would reveal a biochemical property necessary to cytotoxicity.
Dec 01, 2008 · The traceless Staudinger ligation was designed by Raines and coworkers and Bertozzi and coworkers to generate a native peptide bond from an azide and a phosphine (Scheme 3II). Since its first disclosure, the traceless Staudinger reaction has been the subject of extensive studies to better understand the mechanism in order to optimize the Matthew B. Soellner, Annie Tam, and Ronald T. Raines. Staudinger ligation of peptides at non-glycyl residues J. Org. Chem. 2006 71 9824-9830. PubMed. Matthew B. Soellner, Bradley L. Nilsson, and Ronald T. Raines. Reaction mechanism and kinetics of the traceless Staudinger ligation J. Am. Chem. Soc. 2006 128 8820-8828 PubMed. Research Areas(s) 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 tha … 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]
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.
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 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 ).
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.
Full Text A Photo‐Triggered Traceless Staudinger–Bertozzi Ligation Reaction by Hu, Peng and Feng, Tianshi and Yeung, Chi‐Chung and Koo, Chi‐Kin and Lau, Kai‐Chung and Lam, Michael H. W 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. Dec 01, 2008 · The traceless Staudinger ligation was designed by Raines and coworkers and Bertozzi and coworkers to generate a native peptide bond from an azide and a phosphine (Scheme 3II). Since its first disclosure, the traceless Staudinger reaction has been the subject of extensive studies to better understand the mechanism in order to optimize the