Structure of N ⁶-furfurylaminopurine (kinetin) dihydrogenphosphate

Abstract

The crystal structure of kinetin dihydrogenphosphate has been determined at 115 and 293 K. Kinetin dihydrogenphosphate undergoes a polymorphic phase transition at 291.1 K. In both phases the crystal belongs to the triclinic system with the symmetry described by the space group P\bar 1. In the low-temperature phase, the unit cell is doubled along the a axis. There is a dynamic equilibrium between different tautomeric forms of the adenine residue, determined by the distribution of H atoms within the network of hydrogen bonds.

Kinetin—A multiactive molecule

“…The N6-substitution of adenine induce a specific biological (cytokinin) activity which is a result of changes in its chemical and physical characteristics. From the crystal structure analysis of kinetin and benzylaminopurine salts it follows that N1 is not involved in the hydrogen-bonding network [27,35].…”

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N6-Substituted Adenine

“…11,[16][17][18][19][20] By contrast, while N 6 -benzyladenine 21 and kinetin 22 crystallize in the expected 9H-tautomeric form, the N3-protonated 7H-tautomer ( Figure 1) was observed in the crystal structures of their bromide, chloride and dihydrogenphosphate salts. [23][24][25][26] In recent years the influence of hydrogen bonding interactions and molecular recognition on tautomeric and protonation equilibria has received growing interest and a few examples have been reported in the literature, where a noncanonical nucleobase tautomer is stabilized by a properly positioned H bond acceptor. [27][28][29] Salt and co-crystal formation are popular approaches to optimize the physicochemical properties of a pharmaceutically relevant solid without modifying the molecule itself.…”

Tautomerism and hydrogen bonding in guaninium phosphite and guaninium phosphate salts

“…The importance of tautomeric equilibria has been widely recognized since the early work of Watson & Crick (1953). Several models of spontaneous mutation in DNA are based on the existence of minor tautomeric forms (Kwiatkowski & Pullman, 1975;Topal & Fresco, 1976;Cohen et al, 2003;Sló sarek et al, 2006;Guille & Clegg, 2006). In the Watson-Crick base-pairing scheme of nucleic acids, the nucleic acid bases are assumed to have the amino or the lactam structure (see Fig.…”