Solution Conformational Analysis of 2′‐Amino‐2′‐Deoxyadenosine, 3′‐Amino‐3′‐Deoxyadenosine and Puromycin by Pulsed Nuclear‐Magnetic‐Resonance Methods

Abstract

The solution conformation of 2'-amino-2'-deoxyadenosine, 3'-amino-3'-deoxyadenosine, and 3'-amino-3'-deoxy-6-N,N-dimethyladenosine have been determined by nuclear magnetic resonance in aqueous and ammonia solutions. The analysis of the ribose moiety is based on the two-state S in equilibrium N model of Altona and Sundaralingam. Longitudinal proton relaxation time and nuclear Overhauser enchancement measurements have been carried out in order to characterize the orientation of the base relative to the ribose. Those studies indicate that 3'-amino-3'-deoxyadenosine and 3'-amino-3'-deoxy-6-N,N-dimethyladenosine exist in solution preferentially in the N-anti-g + conformations. On the other hand, 2'-amino-2'-deoxyadenosine adopts the S-syn-g +/t conformation families. It appears that the base is restricted to the anti conformation in the first two compounds, while in 2'-amino-2'-deoxyadenosine, one third of the molecules in the S state are in the anti range. These studies corroborate the previously proposed correlations between the N state of the ribose and the anti orientation of the base and between the S state of the ribose and the syn orientation of the base.