By Zoe A. Shabarova, Alexey A. Bogdanov

Sequencing, cloning, transcription - those are yet a couple of key thoughts in the back of the present breathtaking advances in molecular biology and biochemistry. As those equipment continuosly diversify, biochemists desire a sound chemical figuring out to maintain the speed. Chemists starting operating within the molecular biology lab desire an advent to this box from their viewpoint. This ebook serves either: it describes lots of the identified chemical reactions of nucleosides, nucleotides, and nucleic acids in enough element to supply the specified history, and also, the elemental kin among series, constitution and performance of nucleic acids are presented.The first variation of this publication, which was once released in Russian, has instantly turn into a famous typical reference. This moment, completely revised and up to date version, now released in English, is probably going to accomplish an identical place within the foreign medical neighborhood.

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Extra info for Advanced Organic Chemistry of Nucleic Acids

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The amino group in guanosine does not seem to be modified by hydroxylamine and its 0-alkyl derivative. Only hydroxylamine reacts with uridine and only in an alkaline medium. This reaction leads to the rupture of the heterocycle. This is why it will not be considered here, although the reaction is extensively used for specific modification of nucleic acids at uracil units. Another group of nucleophilic reagents is represented by hydrazine and its derivatives. The reactions involving them are conducted in an aqueous medium, their mechanism being heavily dependent on the pH of the latter.

The most typical reaction in this category is amino group acylation (the acylation also involving the hydroxy groups of the carbohydrate moiety). Of the three major nucleosides containing amino groups in the heterocyclic nucleus, cytidine enters into acylation reactions most easily. For selective N-acetylation the reaction is carried out in an alcohol solution with boiling in the presence of an equimolar amount of acetic anhydride. The structure of the acetylation products has been established by U y IR and NMR spectroscopy.

The corresponding 5-amino nucleosides can be obtained by reduction of the 5-nitro derivatives. Heating of uridine together with formaldehyde in the presence of hydrochloric acid leads to its 5-hydroxymethylation. 0 0 I I R R R-ribose residue Under similar conditions, cytidine does not undergo hydroxymethylation (probably because of protonation of the amino group whose positive charge prevents electrophilic substitution). 5-Hydroxymethyluracil is easily formed when the base is hydroxymethylated in an alkaline medium.

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