Abstract
RECENT spectroscopic work has shown that in aqueous solution pyrimidines and purines form vertical stacks with no evidence of in-plane hydrogen-bonding between pairs of bases1,2. The conformations of polynucleotides in aqueous solution are probably largely determined by the interactions responsible for the vertical stacking of mono-meric species3. In non-aqueous solution, vertical stacking is much less important1,4, and studies of mixtures of the nucleic acid bases indicate specific hydrogen-bonding between those pairs of bases that are complementary in DNA4–10. In solvents which are not hydrogen-bond donors, regardless of polarity, the association constant for the guanine–cytosine pair is several times greater than that for the adenine–thymine (uracil) pair, but in both cases the mixed complex is preferred to a mixture of self-dimers; mixtures of non-complementary bases show no association, although mixed hydrogen-bonded pairs can in principle be drawn.
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Chan, S. I., Schweizer, M. P., Ts'O, P. O. P., and Helmkamp, G. K., J. Amer. Chem. Soc., 86, 4182 (1966).
Lord, R. C., and Thomas, G. J., Biochim. Biophys. Acta, 142, 1 (1967).
DeVoe, H., and Tinoco, I., J. Mol. Biol., 4, 500 (1962).
Shoup, R. R., Miles, H. T., and Becker, E. D., Biochem. Biophys. Res. Commun., 23, 194 (1996).
Katz, L., and Penman, S., J. Mol. Biol., 15, 220 (1966).
Pitha, J., Jones, R. N., and Pithova, P., Canad. J. Chem., 44, 1045 (1966).
Kyogoku, Y., Lord, R. C., and Rich, A., J. Amer. Chem. Soc., 89, 496 (1967).
Kyogoku, Y., Lord, R. C., and Rich, A., Proc. US. Nat. Acad. Sci., 57, 250 (1967).
Küchler, E., and Derkosch, J., Z. Naturforsch., 21 b, 209 (1966).
Binford, J. S., and Holloway, D. M., J. Mol. Biol., 31, 91 (1968).
For some evidence see Freese, Freese, E. B., and Freese, E., Proc. US. Nat. Acad. Sci., 57, 650 (1967).
Koch, A., and Miller, C., J. Theoret. Biol., 8, 71 (1965). Kubitschek, H. E., and Henderson, T. R., Proc.US Nat. Acad. Sci., 55, 512 (1966).
Phillips, J. H., and Brown, D. M., Prog. Nucleic Acid Res., 7, 387 (1967).
Janion, C., and Shugar, D., Acta Biochim. Polon., 12, 338 (1965).
Brown, D. M., Hewlins, M. J. E., and, Schell, P., J. Chem. Soc., (C), 1925 (1968.)
Brown, D. M., and Hewlins, M. J. E., J. Chem. Soc., 2050 (1968).
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BROWN, D., HEWLINS, M. Hydrogen-bond Association of N(4)-Hydroxycytosine with Purines. Nature 221, 656–657 (1969). https://doi.org/10.1038/221656a0
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DOI: https://doi.org/10.1038/221656a0
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