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The synthesis of a series of 2′-deoxyuridine analogues modified at the 5-position and a series of 2′-deoxypurines modified at the 8-position is described. Ultraviolet melting studies have been used to assess the stability of DNA duplexes 12- and 8-residues in length that contain these modifications. Of those modified residues which have been incorporated into oligonucleotides, 5-(prop-1-ynyl)-2′-deoxyuridine is found to impart the greatest increase in stability on the DNA duplexes studied. Thermodynamic analyses show that the reason for this increase in stability arises from a decrease in enthalpy which is related to the DNA base stacking process. We suggest that the degree of stabilisation imparted by the propyne moiety may be sequence dependent.

Original publication




Journal article


Journal of the Chemical Society - Perkin Transactions 1

Publication Date



1131 - 1138