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Chemistry of Nucleosides and Nucleotides: Volume 1 by Tohru Ueda (auth.), Leroy B. Townsend (eds.)

By Tohru Ueda (auth.), Leroy B. Townsend (eds.)

The current quantity is the 1st of a projected four-volume treatise. This quantity includes the subsequent chapters: "Synthesis and response of Pyrimidine Nucleosides," "Synthesis and homes of Purine Nucleosides and Nucleotides," and "Synthesis and houses of Oligonucleotides." those 3 chapters have been chosen for inclusion in quantity I as the parts have supplied the foundation and impetus for the initiation and improvement of the opposite components of study, with a view to be defined in next volumes. every one bankruptcy is very complete in nature and will supply a prepared reference resource for not just the amateur but additionally the skilled investigator or researcher. The chapters were ready through authors with substantial adventure in every one specific sector of study, and this has led to a lucid presentation of every well-defined zone. those volumes have been designed with medicinal chemists, medicinal natural chemists, natural chemists, carbohydrate chemists, actual chemists, and organic chemists in brain. even though, as a result great contemporary curiosity during this study sector due to the organic and chemotherapeutic assessment of nucleosides and nucleotides as anticancer, antiviral, and antiparasitic brokers, those volumes must also be invaluable additions to the libraries of virologists, biochemical pharmacologists, oncologists, and pharmacologists. we want to thank the authors for his or her enthusiasm and help make those volumes to be had to the medical community.

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The oxidation of uracil, thymine, and TMP with hydrogen peroxide and other hydroperoxides proceeded with either a polar or free radical mechanism. - o ~~)~. HOo ~ ,II 05: O N : 0 'II0 )H ,'Pyr -- Pyr dl\ 169 170 47 Synthesis and Reaction of Pyrimidine Nucleosides Near neutrality, the free radical pathway is the most important, whereas at more alkaline pH the predominant reaction was promoted by the nucleophilic attack of the peroxide ion at C-6 of the pyrimidine, which then goes through the 5,6epoxide and 5,6-diol derivative as the degradation intermediate.

Using these conditions, 4-thiouridine was converted to the 4-sulfonate derivative. (290) Studies on the action of hydroxylamine to nucleobases have been conducted extensively. Cytidine gives N 4-hydroxycytidine (104) by two routes. (292) The direct substitution of hydroxylamine at C-4 of cytidine leading to (1M) was also observed, especially in the case of 5-methykytidine. (293) Compound (1M) exists as the tau tomer, uracil-4-oxime (104A), which should behave like thymine in the transcription of the genetic code, thus resulting in a mutation.

The 4-amino group in 5,6-dihydrocytidine is in fact very labile and is rapidly hydrolyzed to dihydrouridine. 305) and a much higher rate of hydrolysis for arabinofuranosylcytosine to arabinofuranosyluracil in comparison to the ribosyl derivative is presumably due to a participation of the 2'-hydroxyl group at the C-6 position. 314) methylamine and aniline, (315) and various aromatic amines (316 )-has been reported. However, these reactions generally require more stringent conditions when compared to the bisulfitemediated exchange ami nations ..

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