Methyl group configuration on acyclic threoninol nucleic acids (a TNAs) impacts supramolecular properties
- PMID:35274662
- DOI: 10.1039/d2ob00266c
Methyl group configuration on acyclic threoninol nucleic acids (a TNAs) impacts supramolecular properties
Abstract
We have synthesized acyclicallo-threoninol nucleic acids (allo-aTNAs), artificial xeno-nucleic acids (XNAs) that are diastereomers of acyclic threoninol nucleic acids (aTNAs), and have investigated their supramolecular properties. Theallo-aTNAs formed homo-duplexes in an antiparallel manner but with lower thermal stability than DNA, whereasaTNAs formed extremely stable homo-duplexes. Theallo-aTNAs formed duplexes with complementaryaTNAs and serinol nucleic acid (SNA). The affinities of L-allo-aTNA were the highest for L-aTNA and the lowest for D-aTNA, with SNA being intermediate. The affinities of D-allo-aTNA were the reverse. Circular dichroism measurements revealed that L- and D-allo-aTNAs had weak right-handed and left-handed helicities, respectively. The weak helicity ofallo-aTNAs likely explains the poor chiral discrimination of these XNAs, which is in contrast toaTNAs that have strong helical orthogonality. Energy-minimized structures of L-allo-aTNA/RNA and L-allo-aTNA/L-allo-aTNA indicated that the methyl group on theallo-aTNA strand is unfavourable for duplex formation. In contrast, the methyl group on L-aTNA likely stabilizes the duplex structurevia hydrophobic effects and van der Waals interactions. Thus, the configuration of the methyl group on the XNA scaffold had an unexpectedly large impact on the hybridization ability and structure.
Similar articles
- Highly stable duplex formation by artificial nucleic acids acyclic threoninol nucleic acid (aTNA) and serinol nucleic acid (SNA) with acyclic scaffolds.Murayama K, Tanaka Y, Toda T, Kashida H, Asanuma H.Murayama K, et al.Chemistry. 2013 Oct 11;19(42):14151-8. doi: 10.1002/chem.201301578. Epub 2013 Aug 23.Chemistry. 2013.PMID:24038212
- Highly stable triple helix formation by homopyrimidine (L)-acyclic threoninol nucleic acids with single stranded DNA and RNA.Kumar V, Kesavan V, Gothelf KV.Kumar V, et al.Org Biomol Chem. 2015 Feb 28;13(8):2366-74. doi: 10.1039/c4ob02328e.Org Biomol Chem. 2015.PMID:25564220
- Kinetics of Strand Displacement Reaction with Acyclic Artificial Nucleic Acids.Makino K, Sugiyama I, Asanuma H, Kashida H.Makino K, et al.Angew Chem Int Ed Engl. 2024 Aug 19;63(34):e202319864. doi: 10.1002/anie.202319864. Epub 2024 Jul 19.Angew Chem Int Ed Engl. 2024.PMID:38840525
- Xeno nucleic acids (XNAs) having non-ribose scaffolds with unique supramolecular properties.Asanuma H, Kamiya Y, Kashida H, Murayama K.Asanuma H, et al.Chem Commun (Camb). 2022 Mar 24;58(25):3993-4004. doi: 10.1039/d1cc05868a.Chem Commun (Camb). 2022.PMID:35107445Review.
- Design and Hybridization Properties of Acyclic Xeno Nucleic Acid Oligomers.Murayama K, Asanuma H.Murayama K, et al.Chembiochem. 2021 Aug 3;22(15):2507-2515. doi: 10.1002/cbic.202100184. Epub 2021 Jun 2.Chembiochem. 2021.PMID:33998765Review.
Publication types
MeSH terms
Substances
Related information
LinkOut - more resources
Full Text Sources
Research Materials