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Nucleic Acids Research, 1975, Vol. 2, No. 5 699-706
© 1975

Articles

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

R. C. Bieaney, A. S. Jones and R. T. Walker

Chemistry Department, University of Birmingham Birmingham B15 2TT, UK

Received March 7, 1975. 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.


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