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Synthesis of N-1-alkyl analogues of cyclic inosine diphosphate ribose (cIDPR) by a new solid phase approach
Author(s) -
Giorgia Oliviero,
Stefano D’Errico,
Nicola Borbone,
Jussara Amato,
Vincenzo Piccialli,
Michela Varra,
Gennaro Piccialli,
Luciano Mayol
Publication year - 2008
Publication title -
nucleic acids symposium series
Language(s) - English
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/nrn290
Subject(s) - inosine , chemistry , alkyl , pyrophosphate , stereochemistry , ribose , solid phase synthesis , combinatorial chemistry , polystyrene , agonist , organic chemistry , adenosine , biochemistry , polymer , receptor , enzyme , peptide
Herein we report an efficient solid-phase synthesis of some N-1-alkyl-substituted analogs of cyclic inosine-diphosphate-ribose (cIDPR), a mimic of cyclic ADP-ribose (cADPR) which has been described as an agonist of the cADPR/Ca(2+) 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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