Synthesis and structure of the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic Acid.
The first synthesis of (alphaS,betaS)-beta-hydroxy-alpha-[(methoxycarbonyl)amino]-4,6-dimethyl-9-oxo-3-beta-D-ribofuranosyl-4,9-dihydro-3H-imidazo[1,2-a]purine-7-butanoic acid methyl ester [(alphaS,betaS)-11] has been achieved by OsO(4) oxidation of [S-(E)]-4-[4,6-dimethyl-9-oxo-3-[2,3,5-tris-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-4,9-dihydro-3H-imidazo[1,2-a]purin-7-yl]-2-[(methoxycarbonyl)amino]-3-butenoic acid methyl ester (13) followed by successive gamma-deoxygenation through the cyclocarbonates, separation from the (alphaS,betaR)-isomer by means of flash chromatography, and deprotection. On the other hand, the minor nucleoside of rat liver tRNA(Phe) was isolated on a scale of 100 microg by partial digestion of unfractionated tRNA (1 g) with nuclease P(1), followed by reverse-phase column chromatography, complete digestion with nuclease P(1)/alkaline phosphatase, and reverse-phase HPLC. Comparison of this nucleoside with the synthetic one has unambiguously established its structure to be (alphaS,betaS)-11.
Itaya
Taisuke
T
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan. itaya@mail.p.kanazawa-u.ac.jp
Kanai
Tae
T
D000818:Animals; D008099:Liver / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D012346:RNA, Transfer, Amino Acyl / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D051381:Rats
D009705:Nucleosides; D012346:RNA, Transfer, Amino Acyl