Development of Clickable Triazabutadienes as Cleavable Cross-Linkers

Persistent Link:
http://hdl.handle.net/10150/620964
Title:
Development of Clickable Triazabutadienes as Cleavable Cross-Linkers
Author:
Cornali, Brandon
Issue Date:
2016
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Abstract: This study illustrates the utility of click chemistry in functionalizing triazabutadienes by allowing access to various applications both biological and material based. Triazabutadienes have been shown to trigger the release of highly reactive diazonium species in a pH dependent way when placed in acidic conditions. Electron-rich phenyl systems such as tyrosine residues have been shown to react with diazonium compounds to form stable azo bonds. Modification of these triazabutadiene motifs can functionalize them as linkers or impact solubility; which can allow for target specificity and mild cleavage of linker in order to liberate diazonium near site of interest. Incorporation of azide-alkyne cycloadditions onto these molecules will allow chemical functionalization and cross-linking properties. The 1,2,3-triazole triazabutadiene derivatives are synthesized via Huisgen 1,3-dipolar cycloaddition from alkynyl modifications on the triazabutadiene that are reacted with various azides that show substrate diversity.
Type:
text; Electronic Thesis
Keywords:
Click Chemistry; Triazabutadiene; Chemistry; Bioconjugate Chemistry
Degree Name:
M.S.
Degree Level:
masters
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Jewett, John C.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen
dc.titleDevelopment of Clickable Triazabutadienes as Cleavable Cross-Linkersen_US
dc.creatorCornali, Brandonen
dc.contributor.authorCornali, Brandonen
dc.date.issued2016-
dc.publisherThe University of Arizona.en
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en
dc.description.abstractAbstract: This study illustrates the utility of click chemistry in functionalizing triazabutadienes by allowing access to various applications both biological and material based. Triazabutadienes have been shown to trigger the release of highly reactive diazonium species in a pH dependent way when placed in acidic conditions. Electron-rich phenyl systems such as tyrosine residues have been shown to react with diazonium compounds to form stable azo bonds. Modification of these triazabutadiene motifs can functionalize them as linkers or impact solubility; which can allow for target specificity and mild cleavage of linker in order to liberate diazonium near site of interest. Incorporation of azide-alkyne cycloadditions onto these molecules will allow chemical functionalization and cross-linking properties. The 1,2,3-triazole triazabutadiene derivatives are synthesized via Huisgen 1,3-dipolar cycloaddition from alkynyl modifications on the triazabutadiene that are reacted with various azides that show substrate diversity.en
dc.typetexten
dc.typeElectronic Thesisen
dc.subjectClick Chemistryen
dc.subjectTriazabutadieneen
dc.subjectChemistryen
dc.subjectBioconjugate Chemistryen
thesis.degree.nameM.S.en
thesis.degree.levelmastersen
thesis.degree.disciplineGraduate Collegeen
thesis.degree.disciplineChemistryen
thesis.degree.grantorUniversity of Arizonaen
dc.contributor.advisorJewett, John C.en
dc.contributor.committeememberNjardarson, Jonen
dc.contributor.committeememberGhosh, Indraneelen
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