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.

journal_name

Sci Rep

journal_title

Scientific reports

authors

Wilks TR,O'Reilly RK

doi

10.1038/srep39192

subject

Has Abstract

pub_date

2016-12-16 00:00:00

pages

39192

issn

2045-2322

pii

srep39192

journal_volume

6

pub_type

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