PAPER: Synthesis of rigid homo- and heteroditopic nucleobase-terminated molecules incorporating adenine and/or thymine

Jacobsen M. F., Andersen C. S., Knudsen M. M., Gothelf, K. V.

Org. Lett. 2007, 9, 2851–2854

Centre for DNA Nanotechnology, Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark

Abstract

A series of homo- and heteroditopic thymine- and/or adenine-terminated molecules incorporating rigid aryl or oligo(phenylene ethynylene) linkers has been efficiently synthesized. The key steps involved in the synthesis are the construction of the N-arylated nucleobases using the Chan-Lam-Evans-modified Ullman coupling and their further elaboration using the Sonogashira coupling. Furthermore, the synthesis of a rigid tripodal thymine derivative is reported.

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