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 concepts at the back of the present breathtaking advances in molecular biology and biochemistry. As those tools continuosly diversify, biochemists want a sound chemical knowing to maintain the velocity. Chemists starting operating within the molecular biology lab want an advent to this box from their perspective. This e-book serves either: it describes lots of the identified chemical reactions of nucleosides, nucleotides, and nucleic acids in adequate aspect to supply the specified history, and also, the elemental family among series, constitution and performance of nucleic acids are presented.The first variation of this booklet, which was once released in Russian, has instantly turn into a famous normal reference. This moment, completely revised and up-to-date version, now released in English, is probably going to accomplish an analogous place within the foreign clinical neighborhood.

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At the same time, atoms contributing a single electron to the aromatic system and having a pair of free electrons (endocyclic nitrogen atoms of the pyridine type: N3 of cytosine, N' of adenine, and also N3 and N7 of adenine and guanine) must exhibit a partial negative charge (ti-). Accordingly, it is these atoms that must be affected by electrophilic reagents in the first place. 1 Heterocyclic Buses 39 Therefore, all of the carbon atoms, except for C5 in pyrimidines, must react with nucleophiles.

J zH0'U do HO OH nehularinc HOCH2 NH3 __c HO OH (6 @ HO OH adenosine Tubemidin. This nucleoside was isolated from a culture of Streptomyces tubecidiens. Its hydrolysis in the presence of the ion-exchange resin Dowex 50 gives 7-deazaadenine (3) and D-ribose. The absorption spectrum of tubercidin in the UV region coincides with that of synthetic 9-methyl-7-deazaadenine (4), which indicates that the carbohydrate moiety in the tubercidin molecule (5) is linked with the nitrogen in the position 9 (P).

However, unlike uridine, it is extremely stable under conditions of acid hydrolysis, which explains why attempts to break it down into components failed for quite some time. The UV absorption spectrum of the 24 1 Structure of Nucleosides compound differed from that of uridine and 1-alkyluracils and was closely similar to that of 5-hydroxymethyluracil. These findings had led to a conclusion that the “fifth nucleoside” is a derivative of uracil, yet, in contrast to the latter, represents a C-glycoside with glycosidic bonding at C5 or C6 in the pyrimidine ring.

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