Solid-Phase Synthesis of a New Diphosphate 5-Aminoimidazole-4-carboxamide Riboside (AICAR) Derivative and Studies toward Cyclic AICAR Diphosphate Ribose 英文参考文献.docVIP
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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 英文参考文献
Molecules 2011, 16, 8110-8118; doi:10.3390/moleculeOPEN 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) mimic.
Keywords: AICAR; cADPR; solid-phase synthesis
1. Introduction
Modified nucleosides and nucleotides are among the most studied biomolecules due to their
numerous biological and pharmacological applications. Apart from being the genomic building blocks,
nucleosides interact with roughly one-third of the protein classes in the human genome, including
Molecules 2011, 16
8111
polymerases, kinases, reductases, motor proteins, m
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