56125-51-0Relevant articles and documents
Facile solid-phase synthesis of AICAR 5-monophosphate (ZMP) and its 4-N-Alkyl derivatives
Oliviero, Giorgia,D'Errico, Stefano,Borbone, Nicola,Amato, Jussara,Piccialli, Vincenzo,Piccialli, Gennaro,Luciano, Mayoi
, p. 1517 - 1524 (2010)
We report herein a facile, solid-phase synthesis of 5-aminol-β-D- ribofuranosylimidazole-4-carboxamide-5'-monophosphate (ZMP), a biosynthetic precursor of purine nucleotides, as well as a small collection of its 4-N-alkyl derivatives. The very difficult, direct, chemical phosphorylation of 5-amino-lβ-D-ribofuranosylimidazole-4-carboxamide (AICAR) was circumvented by installing a suitable, fully protected, phos phate group on the 5'-position of A-l-(2,4-dinitrophenyl)inosine, connected to the solid support through the 2',3'-positions, prior to the purine degradation, which led to the 5amino-imidazole-4-ca:rboxamide moiety. A plausible reaction mechanism for the formation of the ZMP imidazole was also reported.