Syntheses and structural studies of calix[4]arene-nucleoside and calix[4]arene-oligonucleotide hybrids.
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
Kim
Su Jeong
SJ
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.
Kim
Byeang Hyean
BH
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
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