Studies on the synthesis of the hypermodified base isolated from rat liver phenylalanine transfer ribonucleic acid.
Oxidation of methyl (S,E)-4-[4,9-dihydro-4,6-dimethyl-9-oxo-1- (phenylmethyl)-1H-imidazo[1,2-alpha]purine-7-yl]-2-[(methoxycarbonyl) amino]-3-butenoate (3) with osmium tetroxide/N-methylmorpholine N-oxide provided a mixture of diastereomers 4 and 7. Hydrogenolysis of the major dihydroxy compound 4 over Pd-C gave beta-hydroxywybutine [[R-(R*,S*)]-1]. The minor isomer 7 was transformed into [S-(R*,R*)]-1 through the cyclic carbonate 8.
D000818:Animals; D007202:Indicators and Reagents; D008099:Liver / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D011688:Purinones / Q000138:chemical synthesis* / Q000302:isolation & purification; D012346:RNA, Transfer, Amino Acyl / Q000032:analysis*; D051381:Rats
D007202:Indicators and Reagents; D011688:Purinones; D012346:RNA, Transfer, Amino Acyl; C019430:hydroxy-Y base