Methyl group configuration on acyclic threoninol nucleic acids (<i>a</i>TNAs) impacts supramolecular properties

Murayama, Keiji; Kashida, Hiromu; Asanuma, Hiroyuki

doi:10.1039/d2ob00266c

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00266c

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Methyl group configuration on acyclic threoninol nucleic acids (aTNAs) impacts supramolecular properties

Keiji Murayama

Hiromu Kashida

Hiroyuki Asanuma

Abstract: We have synthesized acyclic allo-threoninol nucleic acid (allo-aTNA), an artificial xeno-nucleic acid (XNA) that is the diastereomer of acyclic threoninol nucleic acid (aTNA) and have investigated their supramolecular properties. The...

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2023

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Cited by 3 publications

References 42 publications

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Template‐Directed Incorporation of Functional Molecules into DNA

Kanlidere

2023

ChemBioChem

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We report a versatile method for the incorporation of functional molecules into oligonucleotides carrying reactive groups by using a template-directed postsynthetic approach in the solution phase. For this purpose, we prepared oligonucleotides carrying an amino group on the backbone by using an acylic threoninol scaffold. The resulting oligonucleotides could be used to introduce almost any molecule carrying aldehyde, which can be, among other things, a metal-binding ligand or a fluorophore. In our study, we incorporated aldehyde-bearing phenanthroline, a metal-binding ligand, into oligonucleotides by template-directed reversible conjugation. We observed that the use of an abasic sugar site instead of a natural nucleobase in the template strand increased the yield of conjugation and induced selective incorporation of the phenanthroline. This method could lead progress in the development of probes for the recognition of abasic regions in duplex DNA. Moreover, template-directed formation of metal ligand-oligonucleotide conjugates might have potential applications in hybrid biocatalysis for enantioselective transformations.

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Template‐Directed Incorporation of Functional Molecules into DNA

Kanlidere

2023

ChemBioChem

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Functionalization of acyclic xenonucleic acid with modified nucleobases

Murayama

Yamano

Asanuma

2023

Polym J

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Highly Functional Acyclic Xeno Nucleic Acids

Murayama,

Okita,

Asanuma

2023

Bulletin of the Chemical Society of Japan

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In this account, we discuss applications of artificial nucleic acids, acyclic threoninol nucleic acid (aTNA) and serinol nucleic acid (SNA). Seesaw gate and hybridization chain reaction (HCR) circuits composed of left-handed d-aTNA operate correctly. These left-handed circuits are orthogonal to right-handed d-DNA, d-RNA, and l-aTNA, suppressing interference between the circuits. SNA, which does not have a helical preference, can be used as an interface between right- and left-handed oligomers, resulting in selective detection of right-handed d-RNA via left-handed d-aTNA circuits. This detection system is not affected by contamination with natural nucleic acids in bio-samples due to the orthogonality. For chemical primer extension of l-aTNA, chemical ligation by N-cyanoimidazole and a divalent metal cation was investigated. The chemical ligation of l-aTNA was significantly faster and more effective than that of DNA. The chemical primer extension of l-aTNA was achieved using a random trimer pool as ingredients, demonstrating the promise of l-aTNA-based SELEX and artificial genetic systems.

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Methyl group configuration on acyclic threoninol nucleic acids (aTNAs) impacts supramolecular properties

Abstract: We have synthesized acyclic allo-threoninol nucleic acid (allo-aTNA), an artificial xeno-nucleic acid (XNA) that is the diastereomer of acyclic threoninol nucleic acid (aTNA) and have investigated their supramolecular properties. The...

Cited by 3 publications

References 42 publications

Template‐Directed Incorporation of Functional Molecules into DNA

Template‐Directed Incorporation of Functional Molecules into DNA

Functionalization of acyclic xenonucleic acid with modified nucleobases

Highly Functional Acyclic Xeno Nucleic Acids

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