Studies on the Syntheses of the Hypermodified Nucleosides of Phenylalanine Transfer Ribonucleic Acids

Accession number;03A0318143
Title;Studies on the Syntheses of the Hypermodified Nucleosides of Phenylalanine Transfer Ribonucleic Acids
Author; ITAYA TAISUKE (Kanazawa Univ., Faculty of Pharmaceutical Sci., JPN)
Journal Title;Journal of the Pharmaceutical Society of Japan
Journal Code:F0508A
ISSN:0031-6903
VOL.123;NO.5;PAGE.267-283(2003)
Figure&Table&Reference;FIG.19, REF.60
Pub. Country;Japan
Language;Japanese
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 tRNAPhe. 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. (author abst.)
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