The Fine Structure of Cytosine

1962 ◽  
Vol 15 (4) ◽  
pp. 851 ◽  
Author(s):  
DJ Brown ◽  
M Lyall
Keyword(s):  
Aqueous Solution ◽  
Nuclear Magnetic Resonance ◽  
Fine Structure ◽  
Magnetic Resonance ◽  
Nuclear Magnetic Resonance Spectrum ◽  
Tautomeric Form ◽  
Resonance Spectrum ◽  
Ionization Constants ◽  
Recent Formulation ◽  
Related Compounds

The ionization constants and ultraviolet spectra of cytosine, of its appropriately methylated derivatives, and of related compounds are used to indicate that its pre- dominant tautomeric form in aqueous solution is 4-amino-1,2-dihydro-2-oxopyrimidine. This is in sharp contrast to its recent formulation as a zwitterion on the grounds of its nuclear magnetic resonance spectrum.

THE CONFIGURATION AND CONFORMATION OF THYMIDINE

1961 ◽  
Vol 39 (1) ◽  
pp. 116-120 ◽  
Author(s):  
R. U. Lemieux
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Fine Structure ◽  
Magnetic Resonance ◽  
Nuclear Magnetic Resonance Spectrum ◽  
Resonance Spectrum ◽  
Indirect Evidence ◽  
Anomeric Configuration ◽  
Naturally Occurring ◽  
Configuration And Conformation ◽  
Nuclear Magnetic

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.

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