The Fluorescence Property of Dinucleoside Monophosphates Containing Ethenoadenosine and 5, 6-Dihydrouridine Derivatives

Abstract

The role of neighboring nucleotides in the quenching of ethenoadenosine fluorescence as a constituent of dinucleotides is studied. Bisulfite reacts with the uracil moiety of dinucleoside monophosphate, UpεA to yield an addition product, 5, 6-dihydro-6-sulfouridylyl-ethenoadenosine. During the course of the reaction, the fluorescence of ethenoadenosine increases up to 8-fold, to the same intensity as that of monomeric ethenoadenosine. 5, 6-Dihydrouridylyl-ethenoadenosine has a similar fluorescence intensity. These results form evidence that the role played by a neighboring nucleotide in the quenching of ethenoadenosine fluorescence in oligo- or polynucleotides is to generate an aromatic-aromatic interaction between these bases.