inosinic-acid and tetrabutylammonium

The tetrabutylammonium salt of guanosine 5'-monophosphate (5'-GMP) dissolves in DMSO-d6 forming aggregated species which exhibit some properties of reverse micelles. 1H NOESY experiments show that the 5'-GMP adopts the syn conformation about the glycosidic bond. Molecular mechanics calculations reveal a stable structure with this conformation in which the phosphate group and the amino group of the base are in close enough proximity to hydrogen bond. In contrast inosine 5'-monophosphate in DMSO-d6, which has no NH2 group for hydrogen bond stabilization of the syn conformation, is shown by NMR to have the anti structure. Guanosine in DMSO-d6 behaves differently from 5'-GMP. Guanosine adopts the anti conformation and forms a symmetric dimer via hydrogen bonding between the N3 and NH2 of the bases.

Topics: Dimethyl Sulfoxide; Guanosine; Guanosine Monophosphate; Hydrogen Bonding; Inosine Monophosphate; Magnetic Resonance Spectroscopy; Nucleic Acid Conformation; Protons; Quaternary Ammonium Compounds; Solubility

Topics: Adenosine Monophosphate; Chromatography, High Pressure Liquid; Cytidine Monophosphate; Guanosine Monophosphate; Indicators and Reagents; Inosine Monophosphate; Quaternary Ammonium Compounds; Ribonucleotides; Solvents; Tetraethylammonium; Tetraethylammonium Compounds; Uridine Monophosphate; Xanthine; Xanthines