Synthetic analogues of polynucleotides. (Part) XIV. The synthesis of poly (3'-0-carboxymethyl-2'-deoxycytidine) and its interaction with polyinosinic acid.
Poly (3'-O-carboxymethyl-2'-deoxyctidine) (VII) has been synthesised by the polymerisation of 3'-O-carboxymethyl-4-N-phenoxyacety-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'-O-carboxymethyl-5'-O-triphenylmethyl-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 0.2Macetate, 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 degrees. Attempts to form the 3'-O-carboxymethyl derivative of 4-N-phenoxyacetyl-5'-O-'triphenylmethyl-2'-deoxycytidine to give a shorter synthetic route to VII were not successful. 3'-O-Carboxymethyl-2'-deoxycytidine was obtained by removal of thetriphenylmethyl group from III. Attempts to polymerise this compound in concentrated aqueous solution with a water-soluble carbodiimide were not successful.
D003841:Deoxycytidine / Q000031:analogs & derivatives*; D007292:Inosine Nucleotides; D010642:Phenoxyacetates; D011108:Polymers / Q000138:chemical synthesis; D011119:Polynucleotides / Q000138:chemical synthesis; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature; D013730:Terphenyl Compounds
D007292:Inosine Nucleotides; D010642:Phenoxyacetates; D011108:Polymers; D011119:Polynucleotides; D013730:Terphenyl Compounds; D003841:Deoxycytidine