Syntheses and structural studies of calix[4]arene-nucleoside and calix[4]arene-oligonucleotide hybrids

Nucleic Acids Research
Su Jeong Kim, Byeang Hyean Kim

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

References

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Citations

Oct 21, 2005·Organic Letters·Young Jun SeoByeang Hyean Kim
Jul 5, 2007·Chemical Communications : Chem Comm·Young Jun SeoByeang Hyean Kim
May 23, 2008·Angewandte Chemie·Mehran Nikan, John C Sherman
Jul 7, 2009·Bioorganic & Medicinal Chemistry Letters·Dmitry O KoltunJeff Zablocki
Dec 24, 2005·Chemical Communications : Chem Comm·Young Jun Seo, Byeang Hyean Kim
Mar 11, 2017·The Journal of Organic Chemistry·Kenji D OkochiWei Zhang
Sep 27, 2018·Chemical Communications : Chem Comm·X ZhouJ Jayawickramarajah
Jan 25, 2008·Bioscience Reports·Abdul GbajKenneth T Douglas
May 24, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Grazia M L ConsoliCorrada Geraci
Aug 19, 2007·Organic Letters·Sean P BewSunil V Sharma
Oct 28, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·By Sudhir HusaleAndras Kis

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