Boronic Acid-Functionalized Macromolecules for Facile Preparation of Complex Bioconjugates

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dc.contributor.advisorBall, Zachary Ten_US
dc.creatorSwierczynski, Michael Jen_US
dc.date.accessioned2022-09-23T16:07:27Zen_US
dc.date.available2023-02-01T06:01:14Zen_US
dc.date.created2022-08en_US
dc.date.issued2022-07-26en_US
dc.date.submittedAugust 2022en_US
dc.date.updated2022-09-23T16:07:27Zen_US
dc.description.abstractThe conjugation of macromolecules to proteins can offer a variety of benefits from enhanced in vivo stability of protein-polymer conjugates to targeted delivery of protein-antibody conjugates. Transition-metal mediated bioconjugation with boronic acids has been shown to effectively modify natural proteins site-selectively under mild conditions with accessible reagents, though has been limited to small molecule conjugation. This thesis is on the development of boronic acid based bioconjugation methods for protein-macromolecule bioconjugation. The first two chapters review developments in protein-polymer and boronic acid bioconjugation chemistry. The first chapter details protein-polymer conjugation techniques with a focus on direct conjugation of functionalized polymers onto natural amino acids of proteins. The second chapter discusses protein bioconjugation strategies utilizing boronic acids as the warhead. The development of protein-macromolecule bioconjugates with boronic acid-functionalized macromolecules is covered in chapters 3-5. Polymer-protein conjugates are efficiently prepared via Ni(II) mediated cysteine arylation with ortho-nitroarylboronic acid functionalized polymers in chapter 3. In chapter 4, hetero-boronic acids containing an ortho-nitroarylboronic acid and a alkenylboronic acid moiety are used to conjugate cysteine containing proteins to dipeptide pyroglutamate-histidine tagged peptides and proteins. Finally, in chapter 5, phenylboronic acid-tagged proteins are reversibly conjugated to salicylhydroxamic acid-functionalized molecules including a polymer and dendrimer.en_US
dc.embargo.terms2023-02-01en_US
dc.format.mimetypeapplication/pdfen_US
dc.identifier.citationSwierczynski, Michael J. "Boronic Acid-Functionalized Macromolecules for Facile Preparation of Complex Bioconjugates." (2022) Diss., Rice University. <a href="https://hdl.handle.net/1911/113231">https://hdl.handle.net/1911/113231</a>.en_US
dc.identifier.urihttps://hdl.handle.net/1911/113231en_US
dc.language.isoengen_US
dc.rightsCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.en_US
dc.subjectbioconjugationen_US
dc.subjectPEGylationen_US
dc.subjectprotein modificationen_US
dc.subjectboronic acidsen_US
dc.subjectcysteineen_US
dc.subjectNickel(II)en_US
dc.titleBoronic Acid-Functionalized Macromolecules for Facile Preparation of Complex Bioconjugatesen_US
dc.typeThesisen_US
dc.type.materialTexten_US
thesis.degree.departmentChemistryen_US
thesis.degree.disciplineNatural Sciencesen_US
thesis.degree.grantorRice Universityen_US
thesis.degree.levelDoctoralen_US
thesis.degree.nameDoctor of Philosophyen_US
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