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Nucleic Acids Symposium Series 2008 52(1):573-574; doi:10.1093/nass/nrn290
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© 2008 Oxford University Press

This article appears in the following Nucleic Acid Symposium Series issue: Joint Symposium of the 18th International Roundtable on Nucleosides, Nucleotides and Nucleic Acids and the 35th International Symposium on Nucleic Acids Chemistry [View the issue table of contents]

Synthesis of N-1-alkyl analogues of cyclic inosine diphosphate ribose (cIDPR) by a new solid phase approach

Giorgia Oliviero1, Stefano D'Errico1, Nicola Borbone1, Jussara Amato1, Vincenzo Piccialli2, Michela Varra1, Gennaro Piccialli*,1 and Luciano Mayol1

1Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli "Federico II", Via D. Montesano 49, I-80131 Napoli, Italy and 2Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli ‘Federico II’, Via Cynthia 4, 80126, Napoli, Italy

*Corresponding Author. E-mail: picciall{at}unina.it

Abstract

Herein we report an efficient solid-phase synthesis of some N-1-alkyl-substituted analogs of cyclic inosinediphosphate-ribose (cIDPR), a mimic of cyclic ADP-ribose (cADPR) which has been described as an agonist of the cADPR/Ca2+ signalling system. The proposed synthetic strategy uses a polystyrene support bearing inosine by a 2',3'-acetal linkage which is converted into several N-1-alkylinosine-bis-phosphate derivatives which in turn were cyclized by a solid-phase pyrophosphate bond formation.


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