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Efficient DNA–Polymer coupling in organic solvents : a survey of amide coupling, Thiol-Ene and Tetrazine–Norbornene Chemistries applied to conjugation of Poly(N-Isopropylacrylamide)
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Wilks, Thomas R. and O’Reilly, Rachel K. (2016) Efficient DNA–Polymer coupling in organic solvents : a survey of amide coupling, Thiol-Ene and Tetrazine–Norbornene Chemistries applied to conjugation of Poly(N-Isopropylacrylamide). Scientific Reports, 6 (1). 39192 . doi:10.1038/srep39192 ISSN 2045-2322.
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Official URL: http://dx.doi.org/10.1038/srep39192
Abstract
A range of chemistries were explored for the efficient covalent conjugation of DNA to poly(N-isopropylacrylamide) (poly(NIPAM)) in organic solvents. Amide coupling and thiol–ene Michael addition were found to be ineffective for the synthesis of the desired products. However, the inverse electron-demand Diels–Alder (DAinv) reaction between tetrazine (Tz) and norbornene (Nb) was found to give DNA–polymer conjugates in good yields (up to 40%) in organic solvents (N,N-dimethylformamide, N,N-dimethylacetamide and N-methyl-2-pyrrolidone), and without the need for a catalyst. Methods for the synthesis of Tz-and Nb- functionalised DNA were developed, along with a post-polymerisation functionalisation strategy for the production of Tz-functionalised polymers.
| Item Type: | Journal Article | ||||||
|---|---|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry Q Science > QP Physiology T Technology > TP Chemical technology |
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| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||
| Library of Congress Subject Headings (LCSH): | DNA polymerases, Organic solvents, Polymerization | ||||||
| Journal or Publication Title: | Scientific Reports | ||||||
| Publisher: | Nature Publishing Group | ||||||
| ISSN: | 2045-2322 | ||||||
| Official Date: | 16 December 2016 | ||||||
| Dates: |
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| Volume: | 6 | ||||||
| Number: | 1 | ||||||
| Article Number: | 39192 | ||||||
| DOI: | 10.1038/srep39192 | ||||||
| Status: | Peer Reviewed | ||||||
| Publication Status: | Published | ||||||
| Access rights to Published version: | Open Access (Creative Commons) | ||||||
| Date of first compliant deposit: | 5 April 2017 | ||||||
| Date of first compliant Open Access: | 10 April 2017 | ||||||
| Funder: | Engineering and Physical Sciences Research Council (EPSRC), University of Warwick |
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