title: [Studies on the syntheses of the hypermodified nucleosides of phenylalanine transfer ribonucleic acids].
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan.
authors.forename: Taisuke
authors.initials: T
authors.lastname: Itaya
mesh_terms: 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
chemical_list: 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