By Zoe A. Shabarova, Alexey A. Bogdanov
Sequencing, cloning, transcription - those are yet a couple of key ideas at the back of the present breathtaking advances in molecular biology and biochemistry. As those equipment continuosly diversify, biochemists want a sound chemical figuring out to maintain the speed. 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 historical past, and also, the elemental kinfolk among series, constitution and performance of nucleic acids are presented.The first variation of this e-book, which used to be released in Russian, has instantly turn into a well-known general 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 medical neighborhood.
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Extra info for Advanced Organic Chemistry of Nucleic Acids
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). 30 1 Structure of Nucleosides The ease of conversion of 5’W-tosyl ester of a tubercidin derivative into N3,5’cyclic nucleoside (heating in acetone) suggests that the glycoside center in the antibiotic has a /3-configuration.
The double bond in pyrimidine nucleosides lends itself readily to hydrogenation. 5,6-Dihydro derivatives are obtained with a good yield in catalytic hydrogenation in the presence of rhodium on aluminum oxide and also when platinum or palladium catalysts are employed. R R K-ribose r e s i d u e In the case of cytidine, the reaction does not stop at the step of addition of one mole of hydrogen, which is followed by a subsequent reduction step. Therefore, when 5,6-dihydrocytidine is the desired product, the process must be carefully controlled.
The behavior of pyrimidine and purine derivatives during the methylation with diazomethane is largely dependent on the reaction conditions. In the absence of protic solvents the predominant process is substitution of a methyl group for the hydrogen atom exhibiting the most acidic properties - that is, substitution at N3 in uracil derivatives (this may be equated with the need for preliminary protonation of diazomethane) and at N' in guanine derivatives. The methylation can be represented by the following scheme: N N I I R R 0 0 R R K-ribose residue If other proton donors are also present in the reaction mixture, the methylation of the pyrimidine or purine ring proceeds at the site with the highest electron density because diazomethane becomes electrophilic in the course of the reaction without participation of the heterocyclic base.
Advanced Organic Chemistry of Nucleic Acids by Zoe A. Shabarova, Alexey A. Bogdanov