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Nucleic Acids Research, 1977, Vol. 4, No. 4 939-953
© 1977

Articles

Proton magnetic resonance studies of 2'-, 3'-, and 5'-deoxyadenosine conformations in solution

E. Westhof, H. Plach, I. Cuno and H.-D. Lüdemann

Instrtut für Biophysik und Physikalische Biochemie, Universitat Regensburg D-8400 Regensburg, GFR

Received February 11, 1977. Proton magnetic resonance studies of 2'-deoxyadenosine (2'-dA), 3'-deoxyadenosine (3'-dA), 5'-deoxyadenosine (5'-dA) and 8-bromo-5'-deoxyadenosine (8-Br-5'-dA) have been carried out in the temperature range between –60° and +40°C for ND3, solutions, +40° and +100°C for D20 solutions, and finally +10° and +60°C for pyridine solutions. The analysis is based on the two-state S{rightleftarrows}N model of the ribose moiety proposed by Altona and Sundaralingam. In all solvents,2'-dA favours slightly the S state of the ribose and the g+ conformer of the exocyclic CH2OH group. However, 3'-dA prefers strongly the N state of the ribose and the g+ conformation. Both the S and N states of the ribose are equally favoured by 5'-dA and 8-Br-5'-dA. Evidence for the existence of an intramolecular hydrogen bond between 0(5') and N3 in purine(ß)-nucle-osides is presented. It is also concluded that cordycepin (3'-dA) exists in solution mainly in the anti conformation of the base relative to the ribose.


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