A Pyrene‐Modified Serinol Nucleic Acid Nanostructure Converts the Chirality of Threoninol Nucleic Acids into Circularly Polarized Luminescence Signals
- 2 September 2021
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 27 (59), 14582-14585
- https://doi.org/10.1002/chem.202102333
Abstract
We herein report a circularly polarized luminescent (CPL) probe that can respond to chirality of nucleic acids. An achiral nanostructure was prepared by hybridization of symmetric serinol nucleic acid (SNA) containing pyrene-modified residues. When chiral oligomers were added that were complementary to the SNA, they induced helicity into the SNA nanowire. Efficient circular dichroism (CD) signal amplification was observed when pyrene was attached to uracil base through a rigid alkynyl linker. Both CPL signals and CD signals were observed that depended on the chirality of added acyclic threoninol nucleic acid ( a TNA) oligomer. This system can be used to convert chirality of chiral biomolecules into chiroptical signals.Funding Information
- Japan Society for the Promotion of Science (JP19K22250, JP20H02858, JP18H03933, JP21H05025, JP20K15399, JP20H05970)
- Japan Agency for Medical Research and Development (20am0401007)
- Asahi Glass Foundation
This publication has 31 references indexed in Scilit:
- Amplification of Chirality by Supramolecular Polymerization of Pyrene OligomersAngewandte Chemie, 2011
- Amplification of Chirality by Supramolecular Polymerization of Pyrene OligomersAngewandte Chemie, 2011
- Control of the Chirality and Helicity of Oligomers of Serinol Nucleic Acid (SNA) by Sequence DesignAngewandte Chemie, 2011
- Control of the Chirality and Helicity of Oligomers of Serinol Nucleic Acid (SNA) by Sequence DesignAngewandte Chemie, 2011
- Unexpectedly Stable Artificial Duplex from Flexible Acyclic ThreoninolJournal of the American Chemical Society, 2010
- Supramolecular PolymerizationChemical Reviews, 2009
- Sergeants‐and‐Soldiers Principle in Chiral Columnar Stacks of Disc‐Shaped Molecules with C3 SymmetryAngewandte Chemie, 1997
- Sequence-Selective Recognition of DNA by Strand Displacement with a Thymine-Substituted PolyamideScience, 1991
- Macromolecular stereochemistry: the out-of-proportion influence of optically active comonomers on the conformational characteristics of polyisocyanates. The sergeants and soldiers experimentJournal of the American Chemical Society, 1989
- Enhanced optical activity associated with chiral 1-(1-hydroxyhexyl)pyrene excimer formationJournal of the American Chemical Society, 1980