Hydrogen bonding abilities of 2,4-dithiouridine derivatives.

The base pairing ability of a di-2,4-thiouridine derivative was studied in carbon tetrachloride solutions by the methods of infrared spectroscopy. The strength of the association by hydrogen bonding was found to decrease in the following order: adenine-uracil, adenine-di-2,4-thiouracil, uracil-uracil, and di-2,4-thiouracil-di-2,4-thiouracil. These findings contrast with the previously demonstrated fact that poly(s2s4U) is strongly self-associated and does not form a complex with poly(A). To correlate these results, it is proposed that long range stabilizing forces are acting between the di-2,4-thiouracil residues in polynucleotide chains. This assumption also explains the existence of an ordered structure in the alternating copolymer poly(s2s4U-A).