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)

Thomas R. Wilks, Rachel K. O'Reilly

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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.
Original languageEnglish
Article number39192
JournalScientific Reports
Volume6
DOIs
Publication statusPublished - 16 Dec 2016

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