Alpha-DNA. IV: Alpha-anomeric and beta-anomeric tetrathymidylates covalently linked to intercalating oxazolopyridocarbazole. Synthesis, physicochemical properties and poly (rA) binding.
A new set of molecules made of an intercalating agent (oxazolopyridocarbazole, OPC) covalently linked through a polymethylene chain of various length to the 3' end of alpha-anomeric or beta-anomeric tetradeoxynucleotides (alpha- or beta-T4) have been synthesized. The beta-thymidylate modified compound (beta-T4C5OPC) is able to interact with the complementary sequence, beta-poly (rA); this interaction is strongly stabilized compared to the parent compound, beta-oligo(dT)4 and is specific for poly (rA). The molecule synthesized from the unnatural alpha-anomer, alpha-T4C5OPC, is also able to interact with poly (rA) leading to the formation of an alpha-beta hybrid stabilized by the energy provided by the OPC moiety. The stoechiometry of the binding reaction shows that an A-T pairing occurs in the alpha-beta heterohybrids. Tm studies reveal that the alpha-beta heterohybrids are more stable than their beta-beta counterparts.
D001483:Base Sequence; D002227:Carbazoles / Q000138:chemical synthesis* / Q000378:metabolism; D004247:DNA / Q000378:metabolism*; D006358:Hot Temperature; D007364:Intercalating Agents / Q000378:metabolism*; D009691:Nucleic Acid Denaturation; D010080:Oxazoles / Q000138:chemical synthesis / Q000378:metabolism; D011061:Poly A / Q000378:metabolism*; D011725:Pyridines / Q000138:chemical synthesis / Q000378:metabolism; D013329:Structure-Activity Relationship; D013942:Thymine Nucleotides / Q000138:chemical synthesis* / Q000378:metabolism
D002227:Carbazoles; D007364:Intercalating Agents; D010080:Oxazoles; D011725:Pyridines; D013942:Thymine Nucleotides; D011061:Poly A; D004247:DNA