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Basic Principles in Nucleic Acid Chemistry. Volume 2 by Paul O. P. Ts'o

By Paul O. P. Ts'o

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Sample text

An equilibrium position is established depending on the concentrations of the reactants, while slower, possibly irreversible processes may also occur [138-143]. The reaction with the nonbasic nucleosides uridine, pseudouridine, and inosine, is very fast in the forward and reverse directions [143]. The reaction therefore may become significant when nucleic acids are studied in presence of formaldehyde. An appreciable fraction of the uracil or thymine residues may, in these circumstances, be derivatized with consequent effects on higher structure, but the derivatives will not appear in any degradation products.

The stability of an alkylated internucleotide linkag will depend very much on whether we are dealing with the deoxyribo- or the ribo- series. In the former, the system will be a normal trialkyl phosphate and thus will be susceptible to neutral or base-catalyzed hydrolysis. This may be quite slow (for some rates, see Cox and Ramsay [365]) and it is likely that the introduced alkyl group will often be the more easily displaced. The ease of base-catalyzed displacement, broadly, is in the order 1° > 2° > 3°; more accurately it reflects the stability of the alkoxide ion formed or, in other words, the acidity of the corresponding alcohol.

Large amounts of iodine can be incorporated into the latter and into poly C with little strand breakage [227]. While iodine reacts very poorly with the common bases it rapidly modifies two of the minor nucleosides of tRNA [233,234]. 7V6-Isopentenyladenosine (150) is converted to the cyclized product (152; X = I) [235]. The formation of the alcohol (153) and the cyclized product (152; X = H) in acid must be mechanistically similar, proceeding through the tertiary carbonium ion (151; X = I or H), or related species.

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