Basic Principles in Nucleic Acid Chemistry. Volume 2 by Paul O. P. Ts'o

By Paul O. P. Ts'o

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Extra resources for Basic Principles in Nucleic Acid Chemistry. Volume 2

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M. Brown 50 CH—O- CH—OH 4 CH I CH—OP CH—OP CH—OP CH—OP I ^ H—CH CH CH CH—NRo CH=NR2 r*ll I 182 181 180 In this section we will first consider work with DNA. A variety of methods are available for removing base residues. In practice the purine residues are readily removed from DNA by mild acid treatment, for example, by HCl or formic acid [322,323]. The product, apurinic acid (183), which itself has suffered chain scission, may then be degraded further by acid [324] or, more cleanly, by an aromatic amine in aqueous formic acid.

Reactions of Polynucleotides and Nucleic Acids 35 for example, electrophilic substitution at C-8 gives the product (140). The reaction proceeds in aqueous solution at pH 7. The structure of the product is proved by its hydrolysis to 141 and the independent synthesis of the latter, from 8-bromoguanine and 2-aminofluorene [213]. It is interesting that in the acid hydrolysis of 140 (R = deoxyribosyl 5'-phosphate) to 141 the lability of the glycosidic linkage is closely similar to that of deoxyguanylic acid, so glycosidic bond cleavage cannot be important for the observed biological effects.

G. REACTIONS WITH PERACIDS Over the years many more or less vigorous oxidizing agents have been applied to nucleic acid components [5]. A number of these are discussed later with reference to the cleavage of internucleotide links (Section D,3). Here we confine ourselves to TV-oxidation, a process which is mild enough to preclude adventitious polynucleotide chain scission. The oxidation of heterocyclic bases to their TV-oxides has been studied intensively [196]. This is so too for the nucleic acid bases, particularly as some of the TV-oxides have been found to be carcinogenic [197].

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