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 homes of Oligonucleotides." those 3 chapters have been chosen for inclusion in quantity I as the components have supplied the root and impetus for the initiation and improvement of the opposite parts of analysis, with the intention to be defined in next volumes. each one bankruptcy is very complete in nature and will offer a prepared reference resource for not just the amateur but in addition the skilled investigator or researcher. The chapters were ready through authors with enormous adventure in each one specific zone of analysis, and this has ended in 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. in spite of the fact that, due to the super fresh curiosity during this examine region due to the organic and chemotherapeutic overview of nucleosides and nucleotides as anticancer, antiviral, and antiparasitic brokers, those volumes must also be beneficial 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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2',3'-O-Isopropylideneuridine is also converted to the 6,5'-O-cyclodihydrouridine (94) via the 6-methoxy-5,6-dihydro derivative by acid treatment. (26~) As is well known, the hydroxylic solvents add to the 5,6 double bond of uridines by the photoirradiation. 266) eN" N~O NH ( ) S N~O ~ ~~ O~ O~ 91 c 0 0 0 0 C NH ~ N~O ~ O~ 92 NH N~O ~ O~ 93 e ot 94 0 NCH, NHCH, ~Ao N~O "O~ ~ "O~ O~ O~ 95 96 The rate of hydroxymethylation of 2',3'-O-isopropylideneuridine at C-5 is accelerated by the free 5' -hydroxyl group.

8, the substitution at C-4 of cytidine is often accelerated by a prior addition of the nucIeophile at the 5,6 double bond. Deamination of cytidine by nitrous acid treatment gives uridine. However, more nitrogen was evolved than was expected in the deamination of cytosine, probably due to the decomposition of the cytosine ring. 271) was superior, as demonstrated in the deamination of 6-methylcytidine to 6-methyluridine. (357) Treatment of 2',3',5'-tri-O-benzoyluridine with phosphorus pentasulfide in pyridine at reflux affords the 4-thiouridine derivative (147) in high yield.

2',3'-O-Isopropylideneuridine is also converted to the 6,5'-O-cyclodihydrouridine (94) via the 6-methoxy-5,6-dihydro derivative by acid treatment. (26~) As is well known, the hydroxylic solvents add to the 5,6 double bond of uridines by the photoirradiation. 266) eN" N~O NH ( ) S N~O ~ ~~ O~ O~ 91 c 0 0 0 0 C NH ~ N~O ~ O~ 92 NH N~O ~ O~ 93 e ot 94 0 NCH, NHCH, ~Ao N~O "O~ ~ "O~ O~ O~ 95 96 The rate of hydroxymethylation of 2',3'-O-isopropylideneuridine at C-5 is accelerated by the free 5' -hydroxyl group.

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