Synthesis of 8-Hydroxypurine Nucleosides

Peroxynitrite reaction products of 3′,5′-di -O- acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine

“…The starting material, 2Ј,3Ј,5Ј-tri-O-Ac-8-oxoGuo, was prepared according to the procedure by Ikehara et al (37), except that the 8-BrGuo was acetylated by using standard procedures (38). IIc then was prepared by reacting 2Ј,3Ј,5Ј-tri-…”

Negative association between serum dioxin level and oxidative DNA damage markers in municipal waste incinerator workers

“…Polymorphrep used for collecting lymphocytes from the blood samples were obtained from Daiichi Pure Chemicals Co., Ltd (Japan), DNA Extractor WB kit was obtained from Wako Pure Chemical Industries Ltd. (Japan), Nuclease P1 was obtained from Yamasa Co., Ltd (Japan), and bacterial alkaline phosphatase (Escherichia coli) was obtained from Takara bio Inc (Japan). Ribonucleoside 8-OH-dG used as a marker for fraction collection was prepared as previously described (Ikehara et al 1965), anion exchange resin MCI GEL CA08F (7 lm, Cl À form) was purchased from Mitsubishi Chemical Corp (Japan) and prepared as previously described before being manually packed in a guard (1.5·50 mm) and main (1.5·150 mm) column for use in HPLC-1 (Kasai 2003). The reversed phase column (Capcell Pak C18, 5 lm, 4.6·250 mm) used in HPLC-2 for analysis of the 8-OH-dG fraction was purchased from Shiseido (Japan).…”

Synthesis and Properties of Purine Nucleosides and Nucleotides

“…When 8-bromoguanosine was treated with methanesu[fonyl chloride in pyridine, it was found that this much more reactive reagent introduced a mesyl group at both 5' and 2' (~40 % yield). (362) Sulfonylation of nucleotides in pyridine is unsatisfactory because of the poor solubility of the nucleotides. However, Ikehara and co-workers found that 5'-AMP in aqueous sodium hydroxide gave up to a 60% yield of2'-0-p-to This example of the formation of an anhydronucleoside and the methods described in Section 3.1.3 are important procedures in the inversion of hydroxyl groups on the carbohydrate moiety.…”

“…Nature has provided us an excellent example of this class of compounds in the nucleoside Some excellent new chemistry has been introduced by the reaction of 2'-deoxy-5'-0-trityladenosine (361) with triphenylphosphane/diethyl azodicarboxy late and NH 3 . The reaction proceeds without neighboring-group participation and with inversion of configuration to yield 9-(3-azido-2,3-dideoxy-5-0-trityl-p-D-Ihreo-pentofuranosyl)adenine (362). (38)) The method could potentially be useful for the synthesis of other modified xylonucleosides.…”

“…Ring opening of (582) with sodium azide occurs at the 2' position to give 2'-azido-8-oxoadenosine(ribo configuration). (640) When 8,3' -anhydro-9-( 5-O-p-toluenesulfonyl-p-o-xylofuranosyl )-8-mercaptoadenine (597) was treated with NaSH, a mixture of 9-(3,5-dideoxy-3,5-dimercapto-p-o-xylofuranosyl)-8-mercaptoadenine (598) and the corresponding 8,3'-anhydro derivative (599) were obtained. This result was rationalized by invoking an initial formation of the sulfonium intermediate (600).…”