By Zoe A. Shabarova, Alexey A. Bogdanov
Sequencing, cloning, transcription - those are yet a couple of key thoughts at the back of the present breathtaking advances in molecular biology and biochemistry. As those equipment continuosly diversify, biochemists want a sound chemical realizing to maintain the speed. Chemists starting operating within the molecular biology lab desire an creation to this box from their standpoint. This booklet serves either: it describes many of the identified chemical reactions of nucleosides, nucleotides, and nucleic acids in adequate aspect to supply the specified heritage, and also, the elemental family among series, constitution and performance of nucleic acids are presented.The first version of this ebook, which was once released in Russian, has instantly turn into a well-known general reference. This moment, completely revised and up to date variation, now released in English, is probably going to accomplish an analogous place within the overseas medical neighborhood.
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Additional info for Advanced Organic Chemistry of Nucleic Acids
Continued). (Continued). j 6-N-(N-Threonylcarbony1)adenosine t6 A 6-N-[N-Threonylcarbonyltri(hydroxamethyl)arninomethyl]adenosine Nf 2’-O-Methyladenosine (9-/3-~-2’-O-Methyl ribofuranosyladenine) Am Inosine (9-/3-~ribofuranosylhypoxanthine) I 1-Methylinosine (9-/3-o-ribofuranosyl-lmethylhypoxanthine) m 1I I HO C O N H C ( C H 2 0 H ) 3 I I CH3CHCHNHCO CI f i (6 I In addition, the proton of hydroxyl at C2’ is substituted by CH3 I 21 1 Structure of Nucleosides 22 %able 1-5. (Continued). 9 Pseudouridine 23 Table 1-6.
9 Pseudouridine 25 CH20H O N H H The results of NMR spectroscopy, attesting to presence of a proton at C6 in pseudouridine and its absence at C5, corroborated the findings of the preceding studies. The structure of pseudouridine, just as that of 5-~-ribofuranosyluracil, was also confirmed by synthesis. The configuration of the glycoside center was established in the usual manner: 0 0 Thus, pseudouridine is a 5-~-~-ribofuranosyluracil. Given below are the commonly recognized structural formula and abbreviated symbols of this nucleoside: 0 K HN, 2,NH o(J t T HO 1 OH 0H T HO OH yl or Y U Some RNAs have also been found to contain 2’-O-methylpseudouridine (designated by the abbreviated symbol W m) .
Free halogens in a nonaqueous medium trigger direct substitution for the hydrogen (at C5)in pyrimidine nucleosides: The reaction proceeds under mild conditions with a practically quantitative yield. This has been used to obtain 5-chloro and 5-bromo derivatives of uridine and cytidine. Iodination requires much more vigorous conditions - with heating and the presence of nitric acid which seems to be necessary to remove the hydrogen iodide reducing the iodo derivative produced during the reaction.