Modern tools for the chemical ligation and synthesis of

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 Feb 01, 2009 · Recently, we reported on the development of water-soluble phosphinothiols that can mediate the traceless Staudinger ligation in water in moderate yields. 10 The most efficacious reagent, bis(p-N,N-dimethylaminoethylphenyl)phosphinomethanethiol (1) , can also evoke transthioesterification to generate phosphinothioesters at the C-terminus of Introduction. Native chemical ligation (NCL) is one of the most powerful and frequently used methods employed in the fields of chemistry and chemical biology1 for the construction of polypeptides and proteins.2 The versatility of the approach has encouraged continued development of surrogates, or “masked forms” of the required peptidyl thioesters,3 such as peptidyl hydrazide,4 peptide N Chemical ligation from O-acyl isopeptides via 8- and 11-membered cyclic transition states Siva S. Panda,a Mohamed Elagawany,a,b Hadi M. Marwani,c Eray Çalışkan,a Mirna El Khatib,a Alexander Oliferenko,a Khalid A. Alamry,c and Alan R. Katritzky*a,c aCenter for Heterocyclic Compounds, Department of Chemistry, Author(s): Jin, Shuaijiang; Brea, Roberto J; Rudd, Andrew K; Moon, Stuart P; Pratt, Matthew R; Devaraj, Neal K | Abstract: Biology utilizes multiple strategies, including sequestration in lipid vesicles, to raise the rate and specificity of chemical reactions through increases in effective molarity of reactants. We show that micelle-assisted reaction can facilitate native chemical ligations Sep 19, 2007 · Recently, the “traceless Staudinger ligation” has emerged as a new peptide ligation strategy for the chemical synthesis of proteins. 1, 11, 12 This method is based on the Staudinger reduction, wherein a phosphine reduces an azide via an iminophosphorane intermediate. 13 The iminophosphorane can be acylated to yield, ultimately, an amide

Traceless ligation of cysteine peptides using selective deselenization. Angew. Chem. Int. Ed. Engl. 49(39), 7049–7053 (2010).Crossref, Medline, CAS, Google Scholar; 79 Malins LR, Payne RJ. Synthesis and utility of β-selenol-phenylalanine for native chemical ligation-deselenization chemistry. Org. Lett. 14(12), 3142–3145 (2012).

Traceless β-mercaptan-assisted activation of valinyl Introduction. Native chemical ligation (NCL) is one of the most powerful and frequently used methods employed in the fields of chemistry and chemical biology1 for the construction of polypeptides and proteins.2 The versatility of the approach has encouraged continued development of surrogates, or “masked forms” of the required peptidyl thioesters,3 such as peptidyl hydrazide,4 peptide N Chemical ligation from O-acyl isopeptides via 8- and 11 General Papers ARKIVOC 2014 (iv) 91-106 Page 91 ©ARKAT-USA, Inc Chemical ligation from O-acyl isopeptides via 8- and 11-membered cyclic transition states Siva S. Panda,a Mohamed Elagawany,a,b Hadi M. Marwani,c Eray Çalışkan,a Mirna El Khatib,a Alexander Oliferenko,a Khalid A. Alamry,c and Alan R. Katritzky*a,c aCenter for Heterocyclic Compounds, Department of Chemistry,

Our traceless chemical ligation strategy enables the labeling of target proteins while maintaining their innate function, thereby alleviating functional perturbations associated with common molecular biology techniques.

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 methanethiol was judged to be the most efficacious known reagent for effecting the traceless Staudinger ligation. Introduction The advent of methodology for the chemoselective ligation of peptide fragments has made proteins accessible targets for total chemical synthesis.1 Already, many proteins have been Traceless definition, having or leaving no trace: a traceless crime. See more. Our traceless chemical ligation strategy enables the labeling of target proteins while maintaining their innate function, thereby alleviating functional perturbations associated with common molecular biology techniques. Water-soluble phosphinothiols for traceless Staudinger ligation and integration with expressed protein ligation A Tam, MB Soellner, RT Raines Journal of the American Chemical Society 129 (37), 11421-11430 , 2007