Synthetic Study of Biologically Related Compounds Using Cellulose Derivatives as a Polymer-support

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1.Synthetic Study of Oligonucleotides : (1)The cellulose acetate derivatives were found to be feasible for the syntheses of DNA-type8-mer and of RNA-type 13-mer. (2)Development of efficient methods for the protection of functional groups involved in pseudouridine (psi), 1-beta-D-ribofuranosylthymine(rT), 5, 6-dihydrouridine(D), and phosphate, led us to successful syntheses of RNA-type 12-mer involving psi and rT, 11-mer involving 5'-terminal phosphate through the polymer-support, and 8-mer involving D through the CPG-support.2.Synthetic Study of 2'-omicron-(alpha- and beta-D-ribofuranosyl)adenosines : The alpha-isomer, known as the key compound of poly(ADP-ribose), and the beta-isomer, found as the corresponding 5'-phosphate located at 64th position of Yeast initiator tRNA^<Met>, were synthesized with high stereoselectivity by the acid-catalyzed coupling reaction of an adenosine 2'-hydroxyl derivative with D-ribofuranosyl derivatives functionalized at their anomeric position.3.Synthetic Study of Oligosaccharides : Novel approaches to glycosylation in terms of acid-catalyzed coupling reaction of a glycosyl acceptor with glycosyl donors bearing 1-phenoxylcarbonate and 1-phenylcarbamate were developed. and the latter was found to be particularly feasible for the synthesis of oligosaccharides such as Le^Y antigenic tetrasaccharide.4.Synthetic Study of Nucleosides Specifically Labeled with Stable Isotopes : Highly diastereoselective syntheses of (2'R)- and (2'S)-[2'-^2H]-2'-deoxyribonucleosides, and efficient method for the syntheses of nucleosides bearing exocyclic amino groups, were labeled with ^<15>N atom, were realized. These products essentially contribute to the NMR spectroscopic study on delicate conformational analysis on interactions of nucleic acid-nucleic acid or nucleic acid-protein etc.