[Studies on the syntheses of the hypermodified nucleosides of phenylalanine transfer ribonucleic acids].
This review highlights the first total synthesis of (alpha S, beta S)-beta-hydroxywybutosine, the identity of which was established with fluorescent nucleoside isolated from rat liver tRNA(Phe). Three general prerequisites for the synthesis of the target are emphasized: construction of new 9-beta-D-ribofuranosyl-3-methylpurines; the first syntheses of optically active gamma-aryl-alpha,beta-unsaturated amino acids; and a new method for hydrogenolysis of glycols through their cyclic carbonates to give the gamma-aryl-beta-hydroxy amino acid derivatives. The mechanism for the formation of cyclic carbonates from reactions of glycols with (COCl)2 and highly selective preparation of the cyclic oxalates are also described.
Itaya
Taisuke
T
Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan.
D000596:Amino Acids / Q000138:chemical synthesis; D002236:Carbohydrate Conformation; D002254:Carbonates; D002625:Chemistry, Organic / Q000379:methods; D003035:Cobalt; D004146:Dioxanes / Q000138:chemical synthesis; D006018:Glycols; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis; D012360:RNA, Transfer, Phe / Q000737:chemistry
D000596:Amino Acids; D002254:Carbonates; D004146:Dioxanes; D006018:Glycols; D009705:Nucleosides; D011684:Purine Nucleosides; D012360:RNA, Transfer, Phe; C467591:wybutosine; D003035:Cobalt; C018021:cobaltous chloride