Highly stable triple helix formation by homopyrimidine (L)-acyclic threoninol nucleic acids with single stranded DNA and RNA
- PMID:25564220
- DOI: 10.1039/c4ob02328e
Highly stable triple helix formation by homopyrimidine (L)-acyclic threoninol nucleic acids with single stranded DNA and RNA
Abstract
Acyclic (L)-threoninol nucleic acid (aTNA) containing thymine, cytosine and adenine nucleobases were synthesized and shown to form surprisingly stable triplexes with complementary single stranded homopurine DNA or RNA targets. The triplex structures consist of two (L)-aTNA strands and one DNA or RNA, and these triplexes are significantly stronger than the corresponding DNA or RNA duplexes as shown in competition experiments. As a unique property the (L)-aTNAs exclusively form triplex structures with DNA and RNA and no duplex structures are observed by gel electrophoresis. The results were compared to the known enantiomer (D)-aTNA, which forms much weaker triplexes depending upon temperature and time. It was demonstrated that (L)-aTNA triplexes are able to stop primer extension on a DNA template, showing the potential of (L)-aTNA for antisense applications.
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
- Formation of i-motifs from acyclic (l)-threoninol nucleic acids.Kumar V, Nguyen TJD, Palmfeldt J, Gothelf KV.Kumar V, et al.Org Biomol Chem. 2019 Sep 7;17(33):7655-7659. doi: 10.1039/c9ob01220f. Epub 2019 Jul 30.Org Biomol Chem. 2019.PMID:31360984
- Unexpectedly stable homopurine parallel triplex of SNA:RNA*SNA and L-aTNA:RNA*L-aTNA.Kamiya Y, Lao S, Ariyoshi J, Sato F, Asanuma H.Kamiya Y, et al.Chem Commun (Camb). 2024 Jan 30;60(10):1257-1260. doi: 10.1039/d3cc05555h.Chem Commun (Camb). 2024.PMID:38175608
- 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.
- Triplex DNA structures.Frank-Kamenetskii MD, Mirkin SM.Frank-Kamenetskii MD, et al.Annu Rev Biochem. 1995;64:65-95. doi: 10.1146/annurev.bi.64.070195.000433.Annu Rev Biochem. 1995.PMID:7574496Review.
Cited by
- Nonenzymatic polymerase-like template-directed synthesis of acyclic L-threoninol nucleic acid.Murayama K, Okita H, Kuriki T, Asanuma H.Murayama K, et al.Nat Commun. 2021 Feb 5;12(1):804. doi: 10.1038/s41467-021-21128-0.Nat Commun. 2021.PMID:33547322Free PMC article.
- Functionalized Acyclic (l)-Threoninol Nucleic Acid Four-Way Junction with High Stability In Vitro and In Vivo.Märcher A, Kumar V, Andersen VL, El-Chami K, Nguyen TJD, Skaanning MK, Rudnik-Jansen I, Nielsen JS, Howard KA, Kjems J, Gothelf KV.Märcher A, et al.Angew Chem Int Ed Engl. 2022 Jun 13;61(24):e202115275. doi: 10.1002/anie.202115275. Epub 2022 Apr 13.Angew Chem Int Ed Engl. 2022.PMID:35352451Free PMC article.
- Fluorogenic thiazole orange TOTFO probes stabilise parallel DNA triplexes at pH 7 and above.Walsh S, El-Sagheer AH, Brown T.Walsh S, et al.Chem Sci. 2018 Aug 1;9(39):7681-7687. doi: 10.1039/c8sc02418a. eCollection 2018 Oct 21.Chem Sci. 2018.PMID:30393529Free PMC article.
Publication types
MeSH terms
Substances
Related information
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials