Synthesis and Properties of 2′4′- and 3′-5′-Linked Ribodinucleoside Monophosphates Containing 2-Aminoadenosine and Uridine

Publisher Website
Google Scholar
Abstract
Self complementary diribonucleoside monophosphates containing 2-aminoadenosine (n2A) and uridine (U) residues, (2′-5′) n2ApU (1), (3′-5′) n2ApU (2), (2′-5′) Upn2A (3) and (3′-5′) Upn2A (4), were synthesized by condensation of suitably protected nucleoside and nucleotide units using dicyclohexylcarbodiimide (DCC). The dimers, (3) and (41, were also obtained from uridine 2′,3′-cyclic phosphate and unprotected 2-aminoadenosine using 2,4,6-triisopropylbenzenesulfonyl chloride (TPS-Cl) as the condensing agent. The conformational properties of these dimers were examined by UV, CD and NMR spectroscopy. The results reveal that the 2′-5′ isomers take a stacked conformation, which contains a larger base-base overlap and is more stable against thermal perturbation with respect to the 3′-5′ isomers. The n2ApU isomers have more stacked structure than the Upn2A isomers.

This publication has 13 references indexed in Scilit: