- 7-(β-D-Ribofuranosyl)-3-methylguanine: Synthesis from guanine and comparative multinuclear NMR studies
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It was shown that in contrast to guanosine, its 7-regioisomer, 7-(β-D-ribofuranosyl)guanine, when subjected to reaction with methyl iodide in DMF containing sodium hydride, promoted the preferential formation of 3-substituted product, whereas 1-methylated
- Baranowski, Daniel,Boryski, Jerzy,Ostrowski, Tomasz
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- Facile, general and productive syntheses of the fluorescent wye (4,9-dihydro-4,6-dimethyl-9-oxo-1H-imidazo[1,2-a]purine) in phenylalanine tRNA, its 2-substituted derivatives and 7-aza analogues
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Novel syntheses of 4,9-dihydro-4,6-dimethyl-9-oxo-1 H-imidazo[1,2-a]purine (Y base skeleton), its 2-substituted derivatives and 7-aza analogues and their fluorescence characteristics in relation to their structures are described.
- Nagmatsu,Yamasaki
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p. 2041 - 2043
(2007/10/02)
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- Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid
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Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (5a) with CNBr in acetate buffer gave the 5-cyanomethylamino derivative 6a, which was cyclized to 3-methyl-guanosine (7) in the presence of NaOEt.Cyclocondensation of 7 with bromoacetone in the presence of K2CO3 provided 3-β-D-ribofuranosylwye (2), the most probable strucure for the fluorescent nucleoside from Torulopsis utilis phenylalanine transfer ribonucleic acid (tRNAPHE).The glycosidic bonds of 2 and 7 have been shown to be unusually subject to cleavage under either acidic or basic conditions, but proved to be less labile under neutral conditions, as had been reported.The base moiety of 2 is also cleaved under basic conditions.Keywords--wyosine; 3-methylguanosine; cyclocondensation; imidazole nucleoside; N-cyanation; base-catalyzed cyclization; glycosidic bond cleavage; ring fission
- Itaya, Taisuke,Matsumoto, Hiroo,Watanabe, Tomoko,Harada, Tsunehiro
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p. 2339 - 2347
(2007/10/02)
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- Improved Synthesis of 3-methylguanine
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An improved procedure for the synthesis of 3-methylguanine (4) from 2,6-diamino-1-methyl-4-pyrimidone (1) is presented. elemental analyses and ultraviolet (UV) and nuclear magnetic resonance (NMR) spectral data are presented for the compounds involved in the reaction sequence.Keywords - 3-methylguanine; 4-pyrimidones; Traube synthesis; nitrosation; reduction; ring clusore; UV; NMR
- Itaya, Taisuke,Shioyama, Chieko,Kagatani, Seiya
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p. 3392 - 3394
(2007/10/02)
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