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Synthesis of a New N 1 ‐Pentyl Analogue of Cyclic Inosine Diphosphate Ribose (cIDPR) as a Stable Potential Mimic of Cyclic ADP Ribose (cADPR)
Author(s) -
Galeone Aldo,
Mayol Luciano,
Oliviero Giorgia,
Piccialli Gennaro,
Varra Michela
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:24<4234::aid-ejoc4234>3.0.co;2-8
Subject(s) - chemistry , pyrophosphate , ribose , intramolecular force , cyclic adp ribose , stereochemistry , nucleotide , inosine , derivative (finance) , phosphate , alkylation , combinatorial chemistry , biochemistry , adenosine , enzyme , cd38 , stem cell , biology , cd34 , gene , financial economics , economics , genetics , catalysis
The new analogue 7 of cADPR ( 1 ), a cyclic nucleotide bis(phosphate) involved in Ca 2+ metabolism, was prepared starting from 2′,3′‐isopropylideneinosine ( 8 ) which was alkylated at N‐1, leading to the intermediate 11 . Bis(phosphorylation) of 11 through two alternative procedures, followed by phosphate deprotection steps, afforded derivatives 15 and 16 , the substrates for the intramolecular pyrophosphate bond formation. Both 15 and 16 were converted into derivative 17 in high yields, which was finally deprotected to give the target compound 7 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)