Co-reporter:Diana C. Knyazeva, Flora W. Kimani, Jean-Laurent Blanche, John C. Jewett
Tetrahedron Letters 2017 Volume 58, Issue 28(Issue 28) pp:
Publication Date(Web):12 July 2017
DOI:10.1016/j.tetlet.2017.05.056
•Mild alkyl diazonium ion formation.•Mild alkylating agent.•Triazabutadiene.•Sulfonic esterification.Alkyl diazonium ions are among the most reactive alkylating agents in the synthetic chemists’ arsenal. That said, there are precious few methods by which one can selectively and safely utilize this chemistry. Herein, we show the use of a bench stable hexyl triazabutadiene as a source of reactive diazonium ions that undergo substitution chemistry with weak nucleophiles, such as carboxylates and even sulfonates. In the absence of a nucleophile, elimination was observed to occur. To overcome issues stemming from side-product inhibition of the reaction, we show that the triazabutadiene can be pre-activated with tosyl isocyanate.Download high-res image (68KB)Download full-size image
Co-reporter:Brandon M. Cornali, Flora W. Kimani, and John C. Jewett
Organic Letters 2016 Volume 18(Issue 19) pp:4948-4950
Publication Date(Web):September 13, 2016
DOI:10.1021/acs.orglett.6b02420
Triazabutadienes can be used to readily generate reactive aryl diazonium ions under mild, physiologically relevant conditions. These conditions are compatible with a range of functionalities that do not tolerate traditional aryl diazonium ion generation. To increase the utility of this aryl diazonium ion releasing chemistry an alkyne-containing triazabutadiene was synthesized. The copper-catalyzed azide–alkyne cycloaddition (“Cu-click”) reaction was utilized to modify the alkyne-containing triazabutadiene and shown to be compatible with the nitrogen-rich triazabutadiene. One of the triazole products was tethered to a fluorophore, thus enabling the direct fluorescent labeling of a model protein.
Co-reporter:Jie He; Flora W. Kimani
Journal of the American Chemical Society 2015 Volume 137(Issue 31) pp:9764-9767
Publication Date(Web):July 27, 2015
DOI:10.1021/jacs.5b04367
Controlling chemical reactivity using light is a longstanding practice within organic chemistry, yet little has been done to modulate the basicity of compounds. Reported herein is a triazabutadiene that is rendered basic upon photoisomerization. The pH of an aqueous solution containing the water-soluble triazabutadiene can be adjusted with 350 nm light. Upon synthesizing a triazabutadiene that is soluble in aprotic organic solvents, we noted a similar light-induced change in basicity. As a proof of concept we took this photobase and used it to catalyze a condensation reaction.
Co-reporter:Flora W. Kimani ;Dr. John C. Jewett
Angewandte Chemie 2015 Volume 127( Issue 13) pp:4123-4126
Publication Date(Web):
DOI:10.1002/ange.201411277
Abstract
Triazabutadienes are an understudied structural motif that have remarkable reactivity once rendered water-soluble. It is shown that these molecules readily release diazonium species in a pH-dependent manner in a series of buffer solutions with pH ranges similar to those found in cells. Upon further development, we expect that this process will be well suited to cargo-release strategies and organelle-specific bioconjugation reactions. These compounds offer one of the mildest ways of generating diazonium species in aqueous solutions.
Co-reporter:Flora W. Kimani ;Dr. John C. Jewett
Angewandte Chemie International Edition 2015 Volume 54( Issue 13) pp:4051-4054
Publication Date(Web):
DOI:10.1002/anie.201411277
Abstract
Triazabutadienes are an understudied structural motif that have remarkable reactivity once rendered water-soluble. It is shown that these molecules readily release diazonium species in a pH-dependent manner in a series of buffer solutions with pH ranges similar to those found in cells. Upon further development, we expect that this process will be well suited to cargo-release strategies and organelle-specific bioconjugation reactions. These compounds offer one of the mildest ways of generating diazonium species in aqueous solutions.
Co-reporter:Ali M. Ahad, Stephanie M. Jensen, and John C. Jewett
Organic Letters 2013 Volume 15(Issue 19) pp:5060-5063
Publication Date(Web):September 23, 2013
DOI:10.1021/ol402404n
A triarylphosphine reagent that reacts with organic azides to install amide-linked diazirines is reported. This traceless Staudinger reagent reacts with complex organic azides to yield amide-linked diazirines, thus expanding the scope of the utility of both azide and diazirine chemistry.
Co-reporter:Stephanie M. Jensen, Celina T. Nguyen, John C. Jewett
Journal of Virological Methods (September 2016) Volume 235() pp:125-130
Publication Date(Web):1 September 2016
DOI:10.1016/j.jviromet.2016.05.017
•A 5-h protocol to purify dengue virus from contaminants, including C6/36 densovirus.•Purification yields infective, intact virion.•Pelleted virus can be re-suspended at desired concentration.Dengue virus (DENV) is a mosquito-transmitted flavivirus that infects approximately 100 million people annually. Multi-day protocols for purification of DENV reduce the infective titer due to viral sensitivity to both temperature and pH. Herein we describe a 5-h protocol for the purification of all DENV serotypes, utilizing traditional gradient-free ultracentrifugation followed by selective virion precipitation. This protocol allows for the separation of DENV from contaminating proteins – including intact C6/36 densovirus, for the production of infective virus at high concentration for protein-level analysis.
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