Issue 12, 1996

Nucleotide complexes with azoniacyclophanes containing phenyl-, biphenyl- or bipyridyl- units

Abstract

Three cyclophanes (1–3) with p-phenyl, p-biphenyl- and m-bipyridyl spacers between diethylenetriamine units are studied by NMR titrations in water (D2O) with naturally occurring mononucleotides in the form of monophosphates. The biphenyl host 1 shows association constants K(in mol dm–3 units) of 2200 with AMP5′, 1270 with the isomeric AMP3′, and smaller constants with G, C and U derivatives. An exception is GMP5′ with 3, which in contrast to most host compounds shows a four-fold stronger binding than AMP5′. Thymidine (TMP5′) is complexed with K= 2050 dm3 mol1 the intracavity immersion of the T methyl substituent is visible also in the observed upfield NMR shifts. With the smaller hosts 2 and 3, constants of approximately 100–200 dm3 mol–1 are observed, indicating essentially salt bridge contributions. Structural conclusions are supported by the observed NMR shieldings and by selected molecular mechanics calculations.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1996, 2597-2600

Nucleotide complexes with azoniacyclophanes containing phenyl-, biphenyl- or bipyridyl- units

K. G. Ragunathan and H. Schneider, J. Chem. Soc., Perkin Trans. 2, 1996, 2597 DOI: 10.1039/P29960002597

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