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Nucleic Acids Research, 1990, Vol. 18, No. 8 2133-2140
© 1990

MOLECULAR BIOLOGY

Biochemical properties of oligo[(+)]-carbocyclic-thymidylates] and their complexes

János Sági, Attila Szemzõ, Judit Szécsi and László Ötvös

Central Research Institute for Chemistry, Hungarian Academy of Sciences PO Box 17, H-1525 Budapest, Hungary

Received November 21, 1989. Revised February 7, 1990. Accepted February 17, 1990.

We report here spectroscopic and biochemical data of a novel series of sugar-modified oligodeoxynucleotides, the carbocyclic oligothymidylates, c(dT)3–20. In c(dT)n a methylene group has been substituted for the oxygen atom of the deoxyribose ring of the natural thymidylate unit. c(dT)10–20 form helical structures, in contrast with oligothymidylates or poly(dT), based on absorbance versus temperature melting profiles. Secondary structure of c(dT)n, where n>10 is assumed to be double helix. In addition to this, c(dT)n forms as a stable duplex with complementary poly(dA) as does parent (dT)n. On the other hand, c(dT)n-containing oligo/poly duplex is nearly inactive either as a template or as a primer in various DNA polymerase systems, and c(dT)n inhibits DNA replication as well. c(dT)n can efficiently be extended by terminal transferase and shows an increased nuclease stability compared to (dT)n. Base-pairing ability and nuclease stability of c(dT)n suggest that (+)-carbocyclic nucleoside-contalning oligomers could be new potential antisense oligodeoxynucleotides.


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