By Paul O. P. Ts'o
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Extra resources for Basic Principles in Nucleic Acid Chemistry. Volume 2
Brown HO OH OH OH OH 142 143 altered by hydrogen-bonding or by being in a base-stacked environment . The reaction of guanine residues in mono- or polynucleotides with the diazonium salt (144) gives 145, a further example of electrophilic substitution at C-8 [219,220]. O A-TS S03- 144 S0 3 NH ^N>-/ w S03- 145 I. HALOGENATION Halogenation of nucleosides is dealt with in detail in Chapter 2, Volume I. Here we refer only to those reactions which are sufficiently mild to be applic able to the nucleic acids themselves.
Their hydrolytic chemistry is exactly as expected from the known chemistry of RNA and DNA [240a]. B. PHOSPHATE DIESTER HYDROLYSIS Simple dialkyl phosphates, considered as analogs of the internucleotide linkage in DNA, are extremely stable to base and, moreover, hydrolysis, when it does occur, probably does so by alkyl-oxygen cleavage. Acidcatalyzed hydrolysis is also slow. Hydrolysis rates are increased dramatically by neighboring-group participation, a matter which has been studied much in recent years though mainly in compounds other than nucleotides .
M. Brown alkylated purines occurs [120,359,360]. Inactivation results from alkylation. Indeed following alkylation by EMS, bacteriophage T4 survival studies show a primary and a delayed inactivation which are reasonably ascribed, respec tively, to the alkylation and the subsequent chain cleavage . Alkylation mutagenesis presents a confused picture [188,362,363]. In addition to the question of the site of alkylation, explanations require consideration, inter alia, of replication and of repair error before and after depurination.
Basic Principles in Nucleic Acid Chemistry. Volume 2 by Paul O. P. Ts'o