Chemoselective modification of peptides and proteins has wide applications in chemical biology and pharmaceutical {development|improvement}. An {efficient|effective} cysteine (Cys) precise modification protocol {via|by way of|through|by means of} rationally {designed|developed|created|made} β-addition of ynamides is reported. The {strong|powerful|robust|sturdy} electron-withdrawing triflyl group {on the|around the} nitrogen atom of ynamides plays a {crucial|essential|vital|critical|important} {role|function|part} for controlling the chemo-, stereo- and regioselectivities of this protocol. {Another|An additional|Yet another|One more|A different|A further} substituent {of the|from the|in the|on the|with the|of your} terminal ynamides {offers|provides|gives|delivers|presents} a {handle|deal with|manage} for functionality diversification. This Cys modification with ynamides proceeds {efficiently|effectively} {in a|inside a|within a} slightly {basic|fundamental|simple|standard} aqueous media (pH {8|eight}) {to provide|to supply} a series of Z-isomer {of the|from the|in the|on the|with the|of your} corresponding conjugated {products|goods|items|merchandise|solutions} with {excellent|superb|outstanding|exceptional|great|fantastic} stereoselectivity (> 99%) and superior stability. {All the|All of the|Each of the} reactive peptide side chain functional groups {such as|like|including|for example|for instance|which include} amino, carboxyl, {primary|main|major|principal|key} amide, and hydroxyl groups, {as well|also|too|at the same time} {as the|because the} unprotected imidazole and indole rings are compatible. This {method|technique|approach|strategy|system|process} displays a broad substrates scope {including|such as|which includes|like} linear and cyclic peptides and proteins. The {potential|possible|prospective} application of this {method|technique|approach|strategy|system|process} in peptide and protein chemical biology was exemplified by Cys-bioconjugation with ynamides containing {different|various|distinct|diverse|unique|distinctive} functional molecules, {including|such as|which includes|like} drug, fluorescent and affinity tags. {In addition|Additionally|Furthermore|Moreover|Also}, this {strategy|technique|method|approach|tactic} {is also|can also be} compatible with click chemistry (performed in {one|1|a single|one particular} pot), which remarkably extends the toolbox for {further|additional} applications. The chemoselective biotinylation of ubiquitin(G47C) variant {with a|having a|using a} biotinylated ynamide, {as well|also|too|at the same time} {as the|because the} regioselective modification of Cys14 and Cys38 in bovine pancreatic trypsin inhibitor (BPTI) {were|had been|have been} {accomplished|achieved} {under|below|beneath} the optimized {conditions|circumstances|situations} and in {high|higher} yield, {without|with out|without having|with no|devoid of|without the need of} perturbation of disulfide bonds. 5-Bromo-7-chloro-1H-indole Order 12135-22-7 custom synthesis PMID:23996047
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