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2 article(s) from Rozners, Eriks

Isoorotamide-based peptide nucleic acid nucleobases with extended linkers aimed at distal base recognition of adenosine in double helical RNA

Grant D. Walby,
Brandon R. Tessier,
Tristan L. Mabee,
Jennah M. Hoke,
Hallie M. Bleam,
Angelina Giglio-Tos,
Emily E. Harding,
Vladislavs Baskevics,
Martins Katkevics,
Eriks Rozners and
James A. MacKay

Beilstein J. Org. Chem. 2025, 21, 2513–2523, doi:10.3762/bjoc.21.193

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Graphical Abstract

Figure 1: (a) Structure of a PNA oligomer with the N-(2-aminoethyl)glycine backbone (in red); (b) Representat...

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Figure 2: Representative extended nucleobase triples through Hoogsteen hydrogen bonding (blue dashed lines). ...

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Figure 3: Evolution of the strategy for U–A recognition.

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Figure 4: Isoorotamide-derived nucleobases for A–U recognition.

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Figure 5: Proposed isoorotamide distal binding (Db) nucleobases designed from the Io5 core. Hydrogen bonding ...

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Scheme 1: Synthesis of the Db1 monomer (8).

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Scheme 2: Synthesis of Db2 monomer 15.

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Scheme 3: Synthesis of Db3 monomer 21.

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Figure 6: Sequences for RNA hairpins and PNA ligands used for binding studies.

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Figure 7: Major-groove view of hydrogen-bonding interactions in the (A) Db1*U–A triplet, (B) Db2*U–A triplet,...

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Full Research Paper

Published 12 Nov 2025

Full text

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

Nikita Brodyagin,
Martins Katkevics,
Venubabu Kotikam,
Christopher A. Ryan and
Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

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Graphical Abstract

Figure 1: Structure of DNA and PNA.

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Figure 2: PNA binding modes: (A) PNA–dsDNA 1:1 triplex; (B) PNA–DNA–PNA strand-invasion triplex; (C) the Hoog...

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Figure 3: Structure of P-form PNA–DNA–PNA triplex from reference [41]. (A) view in the major groove and (B) view ...

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Figure 4: Structures of backbone-modified PNA.

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Figure 5: Structures of PNA having α- and γ-substituted backbones.

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Figure 6: Structures of modified nucleobases in PNA to improve Hoogsteen hydrogen bonding to guanine and aden...

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Figure 7: Proposed hydrogen bonding schemes for modified PNA nucleobases designed to recognize pyrimidines or...

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Figure 8: Modified nucleobases to modulate Watson–Crick base pairing and chemically reactive crosslinking PNA...

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Figure 9: Examples of triplets formed by Janus-wedge PNA nucleobases (blue). R¹ denotes DNA, RNA, or PNA back...

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Figure 10: Examples of fluorescent PNA nucleobases. R¹ denotes DNA, RNA, or PNA backbones.

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Figure 11: Endosomal entrapment and escape pathways of PNA and PNA conjugates.

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Figure 12: (A) representative cell-penetrating peptides (CPPs), (B) conjugation designs and linker chemistries....

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Figure 13: Proposed delivery mode by pHLIP-PNA conjugates (A) the transmembrane section of pHLIP interacting w...

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Figure 14: Structures of modified penetratin CPP conjugates with PNA linked through either disulfide (for stud...

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Figure 15: Chemical structure of C₉–PNA, a stable amphipathic (cyclic-peptide)–PNA conjugate.

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Figure 16: Structures of PNA conjugates with a lipophilic triphenylphosphonium cation (TPP–PNA) through (A) th...

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Figure 17: Structures of (A) chloesteryl–PNA, (B) cholate–PNA and (C) cholate–PNA(cholate)₃.

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Figure 18: Structures of PNA–GalNAc conjugates (A) (GalNAc)₂K, (B) triantennary (GalNAc)₃, and (C) trivalent (...

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Figure 19: Vitamin B₁₂–PNA conjugates with different linkages.

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Figure 20: Structures of (A) neomycin B, (B) PNA–neamine conjugate, and (C) PNA–neosamine conjugate.

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Figure 21: PNA clamp (red) binding to target DNA containing a mixture of sequences (A) PNA binds with higher a...

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Figure 22: Rolling circle amplification using PNA openers (red) to invade a dsDNA target forming a P-loop. A p...

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Figure 23: Molecular beacons containing generic fluorophores (Fl) and quenchers (Q) recognizing a complementar...

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Figure 24: (A) Light-up fluorophores such as thiazole orange display fluorescence enhancement upon binding to ...

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Figure 25: Templated fluorogenic detection of oligonucleotides using two PNAs. (A) Templated FRET depends on h...

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Figure 26: Lateral flow devices use a streptavidin labeled strip on nitrocellulose paper to anchor a capture P...

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Review

Published 19 Jul 2021

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