Solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (AICAR) derivative and studies toward cyclic AICAR diphosphate ribose

Stefano D'Errico; Giorgia Oliviero; Nicola Borbone; Jussara Amato; Vincenzo Piccialli; Michela Varra; Luciano Mayol; Gennaro Piccialli

doi:10.3390/molecules16098110

Solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (AICAR) derivative and studies toward cyclic AICAR diphosphate ribose

Molecules. 2011 Sep 21;16(9):8110-8. doi: 10.3390/molecules16098110.

Authors

Stefano D'Errico¹, Giorgia Oliviero, Nicola Borbone, Jussara Amato, Vincenzo Piccialli, Michela Varra, Luciano Mayol, Gennaro Piccialli

Affiliation

¹ Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131, Napoli, Italy.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aminoimidazole Carboxamide / analogs & derivatives*
Aminoimidazole Carboxamide / chemical synthesis
Cyclic ADP-Ribose / analogs & derivatives*
Cyclic ADP-Ribose / chemical synthesis*
Cyclization
Drug Stability
Magnetic Resonance Spectroscopy
Molecular Structure
Organophosphorus Compounds / chemical synthesis*
Ribonucleotides / chemical synthesis*
Solid-Phase Synthesis Techniques

Substances

Organophosphorus Compounds
Ribonucleotides
Cyclic ADP-Ribose
Aminoimidazole Carboxamide
AICA ribonucleotide