Bioorthogonal cycloadditions with sub-millisecond intermediates.
Tetrazine- and sydnone-based click chemistries have emerged as important bioconjugation strategies with fast kinetics and N2 or CO2 as the only by-product. Mechanistic studies of these reactions have focused on the initial rate-determining cycloaddition steps. The subsequent N2 or CO2 release from t...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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Wiley
2018
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| _version_ | 1826257926671564800 |
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| author | Qing, Y Pulcu, G Bell, N Bayley, J |
| author_facet | Qing, Y Pulcu, G Bell, N Bayley, J |
| author_sort | Qing, Y |
| collection | OXFORD |
| description | Tetrazine- and sydnone-based click chemistries have emerged as important bioconjugation strategies with fast kinetics and N2 or CO2 as the only by-product. Mechanistic studies of these reactions have focused on the initial rate-determining cycloaddition steps. The subsequent N2 or CO2 release from the bicyclic intermediates has been approached mainly through computational studies, which have predicted lifetimes of femtoseconds. In the present study, bioorthogonal cycloadditions involving N2 or CO2 extrusion have been examined experimentally at the single-molecule level by using a protein nanoreactor. At the resolution of this approach, the reactions appeared to occur in a single step, which places an upper limit on the lifetimes of the intermediates of ~80 μs, consistent with the computational work. |
| first_indexed | 2024-03-06T18:25:55Z |
| format | Journal article |
| id | oxford-uuid:07f62f35-21fd-404b-ad41-6720d886f27c |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:25:55Z |
| publishDate | 2018 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:07f62f35-21fd-404b-ad41-6720d886f27c2022-03-26T09:10:17ZBioorthogonal cycloadditions with sub-millisecond intermediates.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:07f62f35-21fd-404b-ad41-6720d886f27cEnglishSymplectic Elements at OxfordWiley2018Qing, YPulcu, GBell, NBayley, JTetrazine- and sydnone-based click chemistries have emerged as important bioconjugation strategies with fast kinetics and N2 or CO2 as the only by-product. Mechanistic studies of these reactions have focused on the initial rate-determining cycloaddition steps. The subsequent N2 or CO2 release from the bicyclic intermediates has been approached mainly through computational studies, which have predicted lifetimes of femtoseconds. In the present study, bioorthogonal cycloadditions involving N2 or CO2 extrusion have been examined experimentally at the single-molecule level by using a protein nanoreactor. At the resolution of this approach, the reactions appeared to occur in a single step, which places an upper limit on the lifetimes of the intermediates of ~80 μs, consistent with the computational work. |
| spellingShingle | Qing, Y Pulcu, G Bell, N Bayley, J Bioorthogonal cycloadditions with sub-millisecond intermediates. |
| title | Bioorthogonal cycloadditions with sub-millisecond intermediates. |
| title_full | Bioorthogonal cycloadditions with sub-millisecond intermediates. |
| title_fullStr | Bioorthogonal cycloadditions with sub-millisecond intermediates. |
| title_full_unstemmed | Bioorthogonal cycloadditions with sub-millisecond intermediates. |
| title_short | Bioorthogonal cycloadditions with sub-millisecond intermediates. |
| title_sort | bioorthogonal cycloadditions with sub millisecond intermediates |
| work_keys_str_mv | AT qingy bioorthogonalcycloadditionswithsubmillisecondintermediates AT pulcug bioorthogonalcycloadditionswithsubmillisecondintermediates AT belln bioorthogonalcycloadditionswithsubmillisecondintermediates AT bayleyj bioorthogonalcycloadditionswithsubmillisecondintermediates |