Synthetic analogues of polynucleotides. Part XIV. The synthesis of poly (3′-0-carboxymethyl-2′-deoxycytidine) and its interaction with polyinosinic acid

Open Access
Publisher Website
Google Scholar
Abstract
Poly (3′-0-carboxymerhyl-2′-deoxycytidine) (VII) has been synthesised by the polymerisation of 3′-0-carboxymethyl-4-N-phenoxyacetyl-2′-deoxycytidine (V) and removal of the phenoxyacetyl groups under acidic conditions. V was obtained by the action of 2,4-dinitrophenyl phenylacetate on 3′-0-carboxymethyl-5′-0-triphenyl-methyl-2′-deoxycytidine (III) followed by removal of the triphenylmethyl group under carefully controlled acidic conditions. The polymer, VII gave a hypochromic effect of about 20% at 250nm when mixed with poly(1)in 0.2M acetate, pH 5.0. It appeared, therefore, that a complex was formed. Upon heating a solution of this complex there was an initial decrease in optical density followed by a much larger increase to give a Tm of about 60°. Attempts to form the 3′-0-carboxymethyl derivative of 4-N-phenoxyaceryl-5′-0-triphenylmethyl-2′-deoxycytidine to give a shorter synthetic route to VII were not successful. 3′-0-Carboxymethyl-2′-deoxycytidine was obtained by removal of the triphenylmethyl group from III. Attempts to polymerise this compound in concentrated aqueous solution with a water-soluble carbodiimide were not successful.