By N. K. Kochetkov, E. I. Budovskii (auth.), N. K. Kochetkov, E. I. Budovskii (eds.)
The examine of nucleic acids is likely one of the so much swiftly constructing fields in smooth technological know-how. The really very important function of the nucleic acids as a key to the certainty of the character of lifestyles is mirrored within the huge, immense variety of released works at the topic, together with many amazing monographs and surveys. The pathways of syn thesis and metabolism of nucleic acid,s and the various and sundry organic capabilities of those biopolymers are tested with the maximum element within the literature. approximately as a lot cognizance has been paid to the macromolecular chemistry of the nucleic acids: elucidation of the dimensions and form in their molecules, the learn of the physicochemical houses in their strategies, and the precise how you can be utilized in such examine. The surveys of the chemistry of nucleic acids that have been released thus far deal nearly totally with their synthesis and, particularly, with the artificial chemistry of monomers (nucleosides and nucleotides) ; much less realization has been paid to the synthesis of poly nucleotides. there's one more hugely very important point of the chemistry of nucleic acids that is nonetheless within the formative level, the examine of the reactivity of nucleic acid macromolecules and their parts. this may make a major contribution to the deter mination of the constitution of those outstanding biopolymers and to the proper realizing in their organic functions.
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Extra info for Organic Chemistry of Nucleic Acids: Part B
Naphthylamine and 9-aminoacridine take place much more slowly. In the last two cases, steric effects probably play an important role in slowing the reaction. other transamination reactions of cytOSine derivatives, which have been carried out under even more vigorous conditions [185, 186], are also known. The discussion of substitutions of the amino group in the cytosine ring would be incomplete without an examination of reactions of the derivatives of 5,6-dihydrocytosine. Many of the reactions of cytidine and, in particular, the reaction with the hydroxylamines examined above, take place through the intermediate formation of dihydro derivatives.
5 SUBSTITIJTION AND ADDITION REACTIONS IN HETEROCYCLIC RINGS end product of the reaction between pyrimidine derivatives and osmium tetroxide was not specially investigated in [108, 109], it can be considered that, at least in the first stages of the reaction, cis-5,6-dihydroxY-5,6-dihydropyrimidines (XXV) are formed. These are products of hydrolysis of the cyclic ester of osmic acid (XXIV): X: o o S 0 4 --+ HN o C11 3 --0, ~ __ N -90 H2 0 o . . Os~ --+ I H 0 R XXIV HN~~~3 ~N~OH o 7 H R xxv R denotes carbohydrate residue The compound 5,6-dihydroxy-5,6-dihydrothymidine was isolated and identified after treatment of thymidine with an aqueous solution of osmium tetroxide in the presence of barium perchlorate .
The results of investigation of the reaction of 4-exo-N-substituted analogues of cytosine with the hydroxylamines can evidently be explained not only by differences in the pKa values of these compounds, but also by the increase in the degree of bonding of the amino group with the nucleus following introduction of alkyl substituents into it. On the other hand, the introduction of a nuclear-bonded substituent in position 5 or 6 of the pyrimidine ring must hinder addition at the C5 - C6 double bond, for additional energy is required to liberate these substituents from bonding.