title: 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).
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.
authors.affiliation: University of Warwick, Department of Chemistry, Coventry, CV4 7AL, UK.
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Wilks
authors.affiliation: University of Warwick, Department of Chemistry, Coventry, CV4 7AL, UK.
authors.forename: Rachel K
authors.initials: RK
authors.lastname: O'Reilly
mesh_terms: D000180:Acrylic Resins / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry*; D063347:Native Polyacrylamide Gel Electrophoresis; D009636:Norbornanes / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D000180:Acrylic Resins; D000577:Amides; D009636:Norbornanes; D012997:Solvents; D013438:Sulfhydryl Compounds; D013777:Tetrazoles; C052970:poly-N-isopropylacrylamide; C046060:2-norbornene; D004247:DNA