Structural properties of modified deoxyadenosine structures in solution. Impact of the gauche and anomeric effects on the furanose conformation

L.H. Koole, H.M. Buck, A. Nyilas, J. Chattopadhyaya

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Samenvatting

A variable temperature high resolution 1H nuclear magnetic resonance study (at 300 or 500 MHz) of the two modified nucleosides 9-(2'-deoxy-ß-D-threo-ribofuranosyl)-adenine (1) and 9-(3'-deoxy-ß-D-threo-ribofuranosyl)-adenine (2) has been performed. It was found that the furanose conformation in 1 and 2 can be best described as a rapid North (N) South (S) equilibrium that is biased toward the N-form. For 1, a marked temperature dependence of the equilibrium was found, whereas the furanose conformation in 2 is virtually insensitive to temperature changes. Comparison of these results with the well-known conformational properties of the natural nucleosides 2'-deoxyadenosine (2'-dA) and 3'-deoxyadenosine (3'-dA) revealed that the net result of the gauche effect and the anomeric effect is of major importance in determining the furanose conformation. A brief discussion in terms of the thermodynamic parameters that govern the N S equilibria in the investigated nucleosides is given.
Originele taal-2Engels
Pagina's (van-tot)2089-2094
Aantal pagina's6
TijdschriftCanadian Journal of Chemistry
Volume65
Nummer van het tijdschrift9
DOI's
StatusGepubliceerd - 1987

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