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Nucleic Acids Research, 1978, Vol. 5, No. 11 4375-4384
© 1978

Articles

Zwitterionic character of nucleotides: possible significance in the evolution of nucleic acids

M. Sundaralingam and P. Prusiner

Department of Biochemistry, College of Agricultural and Life Sciences, University of Wisconsin-Madison Madison, WI, 53706, USA

Received August 7, 1978. X-ray crystallography has shown that the free acids of adenosine 5'- and 3'-monophosphates and of cytidine 5'- and 3'-monophosphates exist as zwitterions in the solid state with protonation of the adenine base at the N(1) site and of the cytosine base at the corresponding site N(3) and the phosphate group negatively charged. In this paper, evidence is presented for the zwitterionic character of the free acids of the monomeric nucleotides guanosine 5'-monophosphate and inosine 5'-monophosphate with protonation of the base at the N(7) site of the imidazole moiety.


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