1',6'-methano carbocyclic thymidine: Synthesis, X-ray crystal structure, and effect on nucleic acid duplex stability

Article abstract of DOI:10.1016/S0040-4039(00)78359-6

The title compound 1 has been synthesized via bicyclic lactone 3 and amine 9 as the key intermediates. X-ray crystallography reveals the bicyclic skeleton of 1 to adopt a boat-like (3'-exo) conformation. Oligodeoxyribonucleosides incorporating up to 10 building blocks 1 in place of natural thymidine are still capable of binding to complementary DNA or RNA, albeit with lower affinity than the unmodified parent compounds.