solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (aicar) derivative and studies toward cyclic aicar diphosphate ribose固相合成新的二磷酸5-aminoimidazole-4-carboxamide核糖甙(爱卡)导数,研究循环爱卡二磷酸核糖.pdfVIP

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solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (aicar) derivative and studies toward cyclic aicar diphosphate ribose固相合成新的二磷酸5-aminoimidazole-4-carboxamide核糖甙(爱卡)导数,研究循环爱卡二磷酸核糖.pdf

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solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (aicar) derivative and studies toward cyclic aicar diphosphate ribose固相合成新的二磷酸5-aminoimidazole-4-carboxamide核糖甙(爱卡)导数,研究循环爱卡二磷酸核糖

Molecules 2011, 16, 8110-8118; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules 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,*, 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; E-Mail: golivier@unina.it; Tel.: +39-081-678540. Received: 1 August 2011; in revised form: 9 September 2011 / Accepted: 13 September 2011 / Published: 21 September 2011 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) mim