Advanced Organic Chemistry of Nucleic Acids by Zoe A. Shabarova, Alexey A. Bogdanov

By Zoe A. Shabarova, Alexey A. Bogdanov

Sequencing, cloning, transcription - those are yet a couple of key strategies in the back of the present breathtaking advances in molecular biology and biochemistry. As those tools 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 publication serves either: it describes lots of the identified chemical reactions of nucleosides, nucleotides, and nucleic acids in enough aspect to supply the specified historical past, and also, the basic relatives among series, constitution and performance of nucleic acids are presented.The first variation of this booklet, which was once released in Russian, has instantly develop into a well-known normal reference. This moment, completely revised and up-to-date version, now released in English, is probably going to accomplish the same place within the foreign clinical neighborhood.

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The structure of the acetylation products has been established by U y IR and NMR spectroscopy. When the reaction is conducted under vigorous conditions (surplus of the acylating agent, high temperature), the acylation involves not only the amino group of the heterocycle but also the heterocyclic nitrogen (to say nothing of the hydroxy groups of the carbohydrate moiety), for example: 1C0C6H5 ' HO HO Benzoylation of deoxyguanosine (and guanosine) under the same conditions gives a similar derivative, for example: n I HO .

The presence of Dribose was proved by hydrazine-induced cleavage of the nucleoside. Thus, it was established that the “fifth nucleoside” differs from uridine only by the nature of its glycosidic bond. It is for this reason that the nucleoside was called pseudouridine. The fact that pseudouridine has the structure of 5-ribofuranosyluracil was established definitively through double oxidation with periodic acid followed by reduction with sodium borohydride - that is, through conversion into 5hydroxymethyluracil.

3-Ethoxybutan-2-on-1-a1reacts just as guanine nucleosides do: OH 0 R R-ribose residue Nucleosides containing amino groups in the heterocycle typically enter into a reaction with nitrous acid, A case in point is adenosine which is converted into inosine in the presence of nitrous acid: R R-ribose residue Deamination of guanosine and cytidine yields, respectively, xanthosine and uridine. The reaction seems to result in the corresponding diazonium salt in which no delocalization of the positive charge takes place and which readily dissociates, just as diazoalkyls, in an aqueous medium giving a hydroxy derivative.

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