title: Solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (AICAR) derivative and studies toward cyclic AICAR diphosphate ribose.
abstract: The solid-phase synthesis of the first example of a new diphosphate AICAR derivative is reported. The new substance is characterized by the presence of a 5'-phosphate group while a second phosphate moiety is installed on a 5-hydroxypentyl chain attached to the 4-N-position of AICAR. Cyclization of the diphosphate derivative by pyrophosphate bond formation allowed for the formation of a novel AICAR-based cyclic ADP-ribose (cADPR) mimic.
authors.affiliation: Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131, Napoli, Italy.
authors.forename: Stefano
authors.initials: S
authors.lastname: D'Errico
authors.forename: Giorgia
authors.initials: G
authors.lastname: Oliviero
authors.forename: Nicola
authors.initials: N
authors.lastname: Borbone
authors.forename: Jussara
authors.initials: J
authors.lastname: Amato
authors.forename: Vincenzo
authors.initials: V
authors.lastname: Piccialli
authors.forename: Michela
authors.initials: M
authors.lastname: Varra
authors.forename: Luciano
authors.initials: L
authors.lastname: Mayol
authors.forename: Gennaro
authors.initials: G
authors.lastname: Piccialli
mesh_terms: D000620:Aminoimidazole Carboxamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D036563:Cyclic ADP-Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D003500:Cyclization; D004355:Drug Stability; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D012265:Ribonucleotides / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D009943:Organophosphorus Compounds; D012265:Ribonucleotides; D036563:Cyclic ADP-Ribose; D000620:Aminoimidazole Carboxamide; C031143:AICA ribonucleotide