7-Methylguanine nucleotides and their structural analogues; protolytic equilibria, complexing with magnesium (II) ion and kinetics for alkaline opening of the imidazole ring

• Published in: Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry Vol. 42; no. 2; p. 86
• Main Authors: Darzynkiewicz, E, Labadi, I, Haber, D, Burger, K, Lönnberg, H
• Format: Journal Article
• Language: English
• Published: Denmark 01-02-1988
• Subjects: Chemical Phenomena; Chemistry, Physical; Guanine - analogs & derivatives; Guanine - analysis; Guanine - chemical synthesis; Guanine Nucleotides - chemical synthesis; Kinetics; Magnesium; Potentiometry; Spectrophotometry, Ultraviolet
• ISSN: 0302-4369
• DOI: 10.3891/acta.chem.scand.42b-0086

First-order rate constants for the alkaline opening of the imidazole ring of several 7-methylguanine nucleotides and their structural analogues were determined. The results obtained suggested that intramolecular interaction between the negatively charged 5'-phosphate group and the positively charged imidazole ring markedly retard the attack of hydroxide ion on the C8 atom of the 7-methylguanine ring. In contrast, hardly any influence on the acidities of the interacting base and phosphate moieties was detectable. No effect on the complexing of the phosphate group with magnesium(II) ion could be detected.