Oligomerization of adenosin-5´-O-ylmethylphosphonate, an isopolar AMP analogue: Evaluation of the route to short oligoadenylates

0345878 - ÚOCHB 2011 RIV US eng J - Journal Article
Pressová, Martina - Buděšínský, Miloš - Markusová Kóšiová, Ivana - Kopecký, V. Jr. - Cvačka, Josef - Kašička, Václav - Šimák, Ondřej - Točík, Zdeněk - Rosenberg, Ivan
Oligomerization of adenosin-5´-O-ylmethylphosphonate, an isopolar AMP analogue: Evaluation of the route to short oligoadenylates.
Biopolymers. Roč. 93, č. 3 (2010), s. 277-289. ISSN 0006-3525. E-ISSN 1097-0282
R&D Projects: GA MŠMT(CZ) LC06077; GA MŠMT(CZ) LC06061; GA AV ČR KAN200520801; GA ČR GA203/09/0820; GA ČR GA202/09/0193
Grant - others:EMIL-FW6(XE) 503569
Institutional research plan: CEZ:AV0Z40550506
Keywords : spontaneous oligomerization * oligoadenylates * phosphonate linkage
Subject RIV: CC - Organic Chemistry
Impact factor: 2.572, year: 2010

In order to prepare a library of short oligoadenylate analogues featuring both the enzyme-stable internucleotide linkage and the 5´-O-methylphosphonate moiety and thus obtain a pool of potential RNase L agonists/antagonists, we studied spontaneous polycondensation of adenosin-5´-O-ylmethylphosphonic acid (pcA), an isopolar AMP analogue, and its imidazolide derivatives employing N,N´-dicyclohexylcarbodiimide under nonaqueousconditions and uranyl ions under aqueous conditions, resp. The RP LC-MS analyses of the reaction mixtures per se, and those obtained after the periodate treatment, along with analyses and separations by capillary zone electrophoresis, allowed for characterization of major linear and cyclic oligoadenylates obtained. Structure of selected compounds was supported, after their isolation, by NMR spectroscopy.
Permanent Link: http://hdl.handle.net/11104/0187057