69471-51-8Relevant academic research and scientific papers
Structure and synthesis of 6-(substituted-imidazol-1-yl)purines: Versatile substrates for regiospecific alkylation and glycosylation at N9
Zhong, Minghong,Nowak, Ireneusz,Cannon, John F.,Robins, Morris J.
, p. 4216 - 4221 (2007/10/03)
X-ray crystal structures of several 6-(azolyl)purine base and nucleoside derivatives show essentially coplanar conformations of the purine and appended 6-(azolyl) rings. However, the planes of the purine and imidazole rings are twisted ～57° in a 2-chloro-6-(4,5-diphenylimidazol-1-yl)purine nucleoside, and a twist angle of ～61° was measured between the planes of the purine and pyrrole rings in the structure of a 6-(2,5-dimethylpyrrol-1-yl) purine nucleoside derivative. Shielding "above" N7 of the purine ring by a proximal C-H on the 6-azolyl moiety is apparent with the coplanar compounds, but this effect is diminished in those without coplanarity. Syntheses of 6-(azolyl)purines from both base and nucleoside starting materials are described. Treatment of 2,6-dichloropurine with imidazole gave 2-chloro-6-(imidazol-1-yl)purine. Modified Appel reactions at C6 of trityl-protected hypoxanthine and guanine derivatives followed by detritylation gave 6-(imidazol-1-yl)- and 2-amino-6-(imidazol-1-yl)purines. Imidazole was introduced at C6 of 2′,3′,5′-tri-O-acetylinosine by a modified Appel reaction, and solvolysis of the glycosyl linkage gave 6-(imidazol-1-yl)purine. Guanosine triacetate was transformed into the protected 2,6-dichloropurine nucleoside, which was subjected to SNAr displacement with imidazoles at C6 followed by glycosyl solvolysis to provide 2-chloro-6-(substituted-imidazol-1-yl)purines. Potential applications of these purine derivatives are outlined.
Studies on Chemical Synthesis of mRNAs. I. Synthesis and Properties of N2-Tritylguanosine Derivatives and Application to Synthesis of pGpUpU
Hata, Tsujiaki,Gokita, Noboru,Sakairi, Nobuo,Yamaguchi, Kazuo,Sekine, Mitsuo,Ishido, Yoshiharu
, p. 2949 - 2955 (2007/10/02)
Trityl (Tr), 4-methoxytrityl (MMTr), and 4,4'-dimethoxytrityl (DMTr) groups were introduced into the 2-amino group of 2',3',5'-tri-O-acetylguanosine by treatment with the corresponding trityl chlorides in pyridine to afford the N2-tritylated guanosine derivatives in high yields.Similarly, the N6-tritylated adenosine derivatives were synthesized.The stability of the three kinds of trityl groups under acidic conditions were described.The MMTr and Tr groups were found to be suitable for the protection of the 2-amino group of guanosine in oligonucleotide synthesis.An appropriately protected N2-tritylguanosine 5-phosphorodithioate derivative was synthesized and utilized for the synthesis of pGpUpU.
NEW GUANOSINE DERIVATIVES: FACILE O6-PHOSPHORYLATION, THIOPHOSPHINYLATION, SULPHONYLATION AND SILYLATION OF GUANOSINE DERIVATIVES BY 4-DIMETHYLAMINOPYRIDINE CATALIZED REACTION
Daskalov, Hristo Petrov,Sekine, Mitsuo,Hata, Tsujiaki
, p. 3899 - 3902 (2007/10/02)
Appropriately protected guanosine derivatives were successfully converted to the corresponding O6-substituted guanosine derivatives by treatment with dialkyl- or diaryl-phosphoryl halides, dialkyl- or diaryl-phosphinothioyl halides, arenesulfon
