Molecules 2011, 16(9), 8110-8118; doi:10.3390/molecules16098110
Article

Solid-Phase Synthesis of a New Diphosphate 5-Aminoimidazole-4-carboxamide Riboside (AICAR) Derivative and Studies toward Cyclic AICAR Diphosphate Ribose

Stefano D’Errico 1 , Giorgia Oliviero 1,2,* email, Nicola Borbone 1 , Jussara Amato 1 , Vincenzo Piccialli 3 , Michela Varra 1 , Luciano Mayol 1  and Gennaro Piccialli 1,2
1 Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131, Napoli, Italy 2 Facoltà di Scienze Biotecnologiche, Università degli Studi di Napoli Federico II, Via D. Montesano, 49, 80131, Napoli, Italy 3 Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cynthia, 4, 80126, Napoli, Italy
* Author to whom correspondence should be addressed.
Received: 1 August 2011; in revised form: 9 September 2011 / Accepted: 13 September 2011 / Published: 21 September 2011
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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.
Keywords: AICAR; cADPR; solid-phase synthesis

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MDPI and ACS Style

D’Errico, S.; Oliviero, G.; Borbone, N.; Amato, J.; Piccialli, V.; Varra, M.; Mayol, L.; Piccialli, G. Solid-Phase Synthesis of a New Diphosphate 5-Aminoimidazole-4-carboxamide Riboside (AICAR) Derivative and Studies toward Cyclic AICAR Diphosphate Ribose. Molecules 2011, 16, 8110-8118.

AMA Style

D’Errico S, Oliviero G, Borbone N, Amato J, Piccialli V, Varra M, Mayol L, Piccialli G. Solid-Phase Synthesis of a New Diphosphate 5-Aminoimidazole-4-carboxamide Riboside (AICAR) Derivative and Studies toward Cyclic AICAR Diphosphate Ribose. Molecules. 2011; 16(9):8110-8118.

Chicago/Turabian Style

D’Errico, Stefano; Oliviero, Giorgia; Borbone, Nicola; Amato, Jussara; Piccialli, Vincenzo; Varra, Michela; Mayol, Luciano; Piccialli, Gennaro. 2011. "Solid-Phase Synthesis of a New Diphosphate 5-Aminoimidazole-4-carboxamide Riboside (AICAR) Derivative and Studies toward Cyclic AICAR Diphosphate Ribose." Molecules 16, no. 9: 8110-8118.

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