A solid-phase approach to the synthesis of N-1-alkyl analogues of cyclic inosine-diphosphate-ribose (cIDPR)

作者：Oliviero Giorgia; D'Errico Stefano; Borbone Nicola; Amato Jussara; Piccialli Vincenzo; Varra Michela; Piccialli Gennaro^*; Mayol Luciano

来源：Tetrahedron, 2010, 66(10): 1931-1936.

DOI：10.1016/j.tet.2010.01.013

We report here an efficient solid-phase synthesis of N-1-alkyl-substituted analogues of cyclic inosine-diphosphate-ribose (cIDPR), a mimic of cyclic ADP-ribose (cADPR). Our synthetic strategy makes use of a polystyrene support to which inosine was bonded through a 2',3'-acetal linkage. Insertion of a ea-hydroxy-polymethylene chain of variable length on N-1, followed by conversion into N-1-alkylinosine-bisphosphate derivatives and cyclization, allowed to obtain analogues of cIDPR of various ring size. The cyclization step was carried out both in solid-phase and in solution by pyrophosphate bond formation. The effect of the N-1-polymethylene chain length on the cyclization yields as well as the reaction conditions, which led to the solid-phase pyrophosphate bond formation, were thoroughly investigated.

• 出版日期2010-3-6