THE CONFIGURATION AND CONFORMATION OF THYMIDINE

Abstract

The nuclear magnetic resonance spectrum for the anomer of the naturally occurring deoxyribonucleoside thymidine allowed a conclusion as to its anomeric configuration through an interpretation of the fine structure observed in the signals for the H1′, H2′, and H2″ atoms. Thus, indirect evidence for the configuration of thymidine was obtained. The nuclear magnetic resonance spectrum of thymidine suggests that the compound possesses considerable conformational purity when dissolved in water since an interpretation of the spectrum leads to the assignment of the plausible conformation wherein all of the large substituents on the furanose ring are in partially staggered orientations with the neighboring atoms.