Solid phase synthesis of nucleobase and ribose modified inosine nucleoside analogues.
The synthesis and the use of new N-1-dinitrophenyl-inosine based solid support is reported. The support, which binds the nucleoside by a 5'-O-monomethoxytrityl function, reacting with N-nucleophiles allowed the synthesis of a small library of N-1 alkylated inosine and AICAR derivatives. Moreover, the obtained supports, after the cleavage of the 2' -3' ribose bond, furnished a set of new N-1 alkylated-2' -3' -secoinosine derivatives in high yields.
Oliviero
Giorgia
G
Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, via D. Montesano 49, I-80131 Naples, Italy. golivier@unina.it
Amato
Jussara
J
D'Errico
Stefano
S
Borbone
Nicola
N
Piccialli
Gennaro
G
Mayol
Luciano
L
D000620:Aminoimidazole Carboxamide / Q000031:analogs & derivatives / Q000737:chemistry; D007288:Inosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012265:Ribonucleotides / Q000737:chemistry; D012266:Ribose / Q000737:chemistry*
C527208:N-1-dinitrophenyl-inosine; D009705:Nucleosides; D012265:Ribonucleotides; D000620:Aminoimidazole Carboxamide; D007288:Inosine; D012266:Ribose; C031143:AICA ribonucleotide