- Oxidation of 9-β-d-ribofuranosyl uric acid by one-electron oxidants versus singlet oxygen and its implications for the oxidation of 8-oxo-7,8-dihydroguanosine
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Uric acid, a cellular antioxidant, undergoes oxidation in the presence of one-electron oxidants as well as singlet oxygen. In the present work, the oxidation pathways and products formed from oxidation of the uric acid nucleoside are compared to the more commonly studied uric acid free base. A wider distribution of products, including allantoin, urea, caffolide, and 5-carboxamido-5-hydroxyhydantoin nucleosides, are formed when the N9 position of uric acid is glycosylated. The oxidation pathways share some features in common with the oxidation of 8-oxo-7,8-dihydroguanosine, but the additional spectrum of products implies that the combination of oxidative and deaminative damage to guanosine may lead to a more complex set of DNA lesions than originally described.
- Nguyen, Khiem V.,Muller, James G.,Burrows, Cynthia J.
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- Nucleotides; Part XXXVI A New Synthesis of 9-(β-D-Ribofuranosyl)uric Acid and its 5'-Monophosphate
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Syntheses for 9-(β-D-ribofuranosyl)uric acid (16) and its 5'-monophosphate 14 have been achieved starting from guanosine and applying the 2-(?-nitrophenyl)ethyl group for protection of the aglycon moiety as well as the phosphate function.A more effficient and direct approach to 14 uses O6,O8-dibenzyl protection and phosphorylation by the Yoshikawa procedure.The various protected intermediates have been characterized by spectroscopic means and elemental analysis.
- Schulz, Bernd S.,Pfleiderer, Wolfgang
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p. 210 - 218
(2007/10/02)
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- Purine and 8-Substituted Purine Arabinofuranosyl and Ribofuranosyl Nucleoside Derivatives as Potential Inducers of the Differentiation of the Friend Erythroleuukemia
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Several antimetabolites have been demonstrated to have the capacity to initiate differentiation in vitro of a variety of leukemic cell lines.To explore the structural requirements for this activity, a series of purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells. 9-(β-D-Arabinofuranosyl)hypoxanthine and 6-(hydroxyamino)-9-(β-D-arabinofuranosyl)purine were effective inducers of maturation, producing 82percent and 74percent benzidine-positive cells, a measure of the number of cells synthesizing hemoglobin. 6-Mercapto-9-(β-D-ribofuranosyl)purine and 6-(methylmercapto)-9-(β-D-ribofuranosyl)purine and their corresponding β-D-arabinofuranosyl derivatives were also effective initiators of maturation, causing approximately 50percent of the cell population to assume a differentiated phenotype.
- Lin, Tai-Shun,Cheng, Jia-Chong,Ishiguro, Kimiko,Sartorelli, Alan C.
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p. 1481 - 1485
(2007/10/02)
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- A NEW SYNTHESIS OF 9-β-D-RIBOFURANOSYLURIC ACID AND ITS 5'MONOPHOSPHATE
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Synthesis for 9-β-D-ribofuranosyluric acid (16) and its 5'-monophosphate 14 starting from guanosine and by applying the p-nitrophenylethyl blocking group are described.
- Schultz, Bernd S.,Pfleiderer, Wolfgang
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p. 5421 - 5424
(2007/10/02)
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