Precise recognition of nucleotides and their derivatives through hydrogen bonding in water by poly(vinyldiaminotriazine)

In water, poly(2-vinyl-4,6-diamino-1,3,5-triazine)(PVDAT) selectively binds the derivatives of thymine and uracil through the formation of three hydrogen bonds with the diaminotriazine (DAT) residues. The nucleotides and dinucleotides are bound much more strongly than are nucleic acid bases, due to the additional interactions of their phosphates with the DAT residues. The binding constant of the thymidine 5′-monophosphate-PVDAT adduct (5400 M^-1) is one of the largest values ever reported for the artificial receptors in protic solvents. In contrast, cytosine and its monophosphate are hardly bound to PVDAT. A water-soluble vinyldiaminotriazine–acrylamide copolymer also forms hydrogen bonds with thymine in water, whereas the corresponding monomers do not. A polymer effect is predominantly important for the molecular recognition through hydrogen bonding in water.