title: Biochemical properties of oligo [(+)-carbocyclic-thymidylates] and their complexes.
abstract: We report here spectroscopic and biochemical data of a novel series of sugar-modified oligodeoxy-nucleotides, 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 greater than 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-containing oligomers could be new potential antisense oligodeoxynucleotides.
authors.affiliation: Central Research Institute for Chemistry, Hungarian Academy of Sciences, Budapest.
authors.forename: J
authors.initials: J
authors.lastname: Sági
authors.forename: A
authors.initials: A
authors.lastname: Szemzõ
authors.forename: J
authors.initials: J
authors.lastname: Szécsi
authors.forename: L
authors.initials: L
authors.lastname: Otvös
mesh_terms: D000042:Absorption; D055598:Chemical Phenomena; D002621:Chemistry; D002942:Circular Dichroism; D004253:DNA Nucleotidylexotransferase / Q000378:metabolism; D004261:DNA Replication; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides / Q000378:metabolism; D043264:Phosphodiesterase I; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism; D011061:Poly A; D011071:Poly T; D011067:Poly dA-dT; D013696:Temperature; D013698:Templates, Genetic; D013938:Thymidine Monophosphate / Q000031:analogs & derivatives / Q000378:metabolism; D013942:Thymine Nucleotides
chemical_list: D009838:Oligodeoxyribonucleotides; D013942:Thymine Nucleotides; D011061:Poly A; D011071:Poly T; D011067:Poly dA-dT; D013938:Thymidine Monophosphate; D004253:DNA Nucleotidylexotransferase; D010727:Phosphoric Diester Hydrolases; D043264:Phosphodiesterase I