19674-60-3Relevant articles and documents
Direct Chemoselective Synthesis of N-3-Substituted Pyrimidinones in a Microwave-Assisted Method
Laxminarayana, Burgula,Kundu, Lal Mohan
, p. 1342 - 1353 (2015)
Synthesis of selectively N-3-substituted pyrimidine nucleobases or pyrimidinones has always been a challenge because of poor regioselectivity and chemoselectivity. In this article we demonstrate a single-step, de novo synthesis of selectively N-3-substitu
Polyfunctional derivatives of isocytosine. Effect of hydration on prototropic tautomerism of 2-(2-hydroxyethyl)amino-6-methylpyrimidin-4(3H)-one
Erkin,Krutikov
, p. 639 - 644 (2008/02/01)
Hydration of 2-(2-hydroxyethyl)amino-6-methylpyrimidin-4(3H)-one forms an equilibrium mixture of 4-oxo-3,4-dihydro and 4-hydroxy tautomers. The intermediate in mutual transitions of these tautomers has a zwitter ionic structure. The equilibrium shifts to the 4-oxo-3,4-dihydro form as the polarity of the medium decreases. 2005 Pleiades Publishing, Inc.
Kinetics and Mechanisms of Hydrolytic Reactions of Methylated Cytidines under Acidic and Neutral Conditions
Kusmierek, Jaroslav,Kaeppi, Rainer,Neuvonen, Kari,Shugar, David,Loennberg, Harri
, p. 196 - 202 (2007/10/02)
First-order constants have been determined for acidic hydrolysis, and for acidic and acid buffer-catalysed, deamination of cytidine and a number of its methylated derivatives.Rate constants for deamination under neutral conditions (frequently referred to as spontaneous deamination) have also been determined.N4-Methyl groups retard both deamination and hydrolysis, the former influence being much larger.A 6-methyl substituent retards deamination even more markedly, but accelerates hydrolysis.The effect of a 5-methyl group on the rates of both reactions is minor.The mechanisms of the deamination reactions under various conditions are discussed on the basis of structural effects, rates of hydrogen exchange at C5 and kinetic α-secondary isotope effects.Relevance of the data to enzyme-catalysed deamination and non-enzymatic deamination of cytosine residues in nucleic acids is briefly discussed.