title: Syntheses and structural studies of calix[4]arene-nucleoside and calix[4]arene-oligonucleotide hybrids.
abstract: We have synthesized three types of calix[4]arene- nucleoside hybrid efficiently by amide bond formation between the amine functional groups of 1,3-diaminocalix[4]arene and the carboxyl groups of thymidine nucleoside derivatives. X-ray crystallography of a homocoupled calix[4]arene-nucleoside hybrid revealed an interesting hydrogen bonding pattern between thymine bases and the amide linkages. We designed the calix[4]arene-oligonucleotide hybrids (5'-AAAAGATATCAAXTTGATATCTTTT-3', 5'-T12-X-T12-3', and 5'-A12-X-T12-3') to be V-shaped oligodeoxyribonucleotides and synthesized them by using a calix[4]arene-nucleoside hybrid (X) as a key building block. Thermal denaturation experiments, monitored by UV spectroscopy at 260 and 284 nm, and circular dichroism spectra of the calix[4]arene-oligonucleotide hybrids suggest that the modified oligonucleotides indeed adopt V-shaped conformations, making them suitable for use as building blocks in the construction of programmed oligonucleotide nanostructures
authors.affiliation: National Research Laboratory, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, San 31 Hyoja Dong, Pohang 790-784, Korea.
authors.forename: Su Jeong
authors.initials: SJ
authors.lastname: Kim
authors.forename: Byeang Hyean
authors.initials: BH
authors.lastname: Kim
mesh_terms: D000577:Amides / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry; D047250:Calixarenes; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004591:Electrophoresis, Polyacrylamide Gel; D006860:Hydrogen Bonding; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C475075:5'-O-TBDPS-thymidine-calix(4)arene-5'-O-TBDPS-thymidine; D000577:Amides; D001952:Bridged-Ring Compounds; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D010636:Phenols; C121325:calix(4)arene; D047250:Calixarenes; D013936:Thymidine