Journal article
Pentafulvene-Maleimide Cycloaddition for Bioorthogonal Ligation
Bioconjugate chemistry, v 32(8), pp 1845-1851
18 Aug 2021
PMID: 34254789
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
The applications of bioconjugation chemistry are rapidly expanding, and the addition of new strategies to the bioconjugation and ligation toolbox will further advance progress in this field. Herein, we present a detailed study of the Diels-Alder cycloaddition (DAC) reaction between pentafulvenes and maleimides in aqueous solutions and investigate the reaction as an emerging bioconjugation strategy. The DAC reactions were found to proceed efficiently, quantitatively yielding cycloadducts with reaction rates ranging up to ∼0.7 M
s
for a series of maleimides, including maleimide-derivatized peptides and proteins. The absence of cross-reactivity of the pentafulvene with a large panel of functional (bio)molecules and biological media further demonstrated the bioorthogonality of this approach. The utility of the DAC reaction for bioorthogonal bioconjugation applications was further demonstrated in the presence of biological media and proteins, as well as through protein derivatization and labeling, which was comparable to the widely employed sulfhydryl-maleimide coupling chemistry.
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Details
- Title
- Pentafulvene-Maleimide Cycloaddition for Bioorthogonal Ligation
- Creators
- Kirsten Platts - University of South AustraliaRobert Michel - Whitney Museum of American ArtElise Green - Whitney Museum of American ArtTodd Gillam - University of South AustraliaMaulik Ghetia - University of South AustraliaNeil O'Brien-Simpson - The University of MelbourneWenyi Li - The University of MelbourneChristopher Blencowe - Whitney Museum of American ArtAnton Blencowe - University of South AustraliaChristopher B Rodell - School of Biomedical Engineering, Science, and Health Systems (1997-)
- Publication Details
- Bioconjugate chemistry, v 32(8), pp 1845-1851
- Publisher
- American Chemical Society; Washington, DC
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- School of Biomedical Engineering, Science, and Health Systems
- Web of Science ID
- WOS:000687162400043
- Scopus ID
- 2-s2.0-85111195027
- Other Identifier
- 991019320404904721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Biochemical Research Methods
- Biochemistry & Molecular Biology
- Chemistry, Multidisciplinary
- Chemistry, Organic