Facile method for the preparation of 7-methyl-8-oxoguanosines as an immunomodulator.
Reaction of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-7-methylguaninium iodide (2a) with hydrogen peroxide in acetic acid gave the corresponding 7-methyl-8-oxoguanosine derivative (3a) in good yield. Deprotection of 3a easily gave 7-methyl-8-oxoguanosine (1), which is well-known as an immunomodulator. Substitution of acetyl group at the N2-position of guanine ring accelerated the oxidation reaction of the 7-methylguaninium iodide.
Department of Biomolecular Science, Faculty of Engineering, Gifu University, Japan. kitade@apchem.gifu-u.ac.jp
Y
Y
Kitade
N
N
Saito
A
A
Kozaki
K
K
Takahashi
C
C
Yatome
Y
Y
Takeda
H
H
Sajiki
K
K
Hirota
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis*; D002855:Chromatography, Thin Layer; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006861:Hydrogen Peroxide / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
D000276:Adjuvants, Immunologic; D009705:Nucleosides; D006151:Guanosine; C050068:7-methyl-8-oxoguanosine; D006861:Hydrogen Peroxide