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

• oligonucleotides (TFOs) [8]. TFOs are utilized in both RNA and DNA recognition [9][10][11][12] and a particular type of TFO, peptide nucleic acid (PNA), has emerged as a promising probe for recognizing ncRNA [13][14][15][16]. The Nielsen lab first designed PNA with the N-(2-aminoethyl)glycine backbone for the

• PNA oligomer with the N-(2-aminoethyl)glycine backbone (in red); (b) Representative monocyclic synthetic nucleobase triples through Hoogsteen hydrogen bonding (blue dashed lines). Watson–Crick hydrogen bonds are in red (dashed lines). Representative extended nucleobase triples through Hoogsteen

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

• positions of the backbone α-Modified PNA: Adding substituents to the N-(2-aminoethyl)glycine backbone has been an obvious starting point for PNA modification. Nielsen and co-workers were the first to replace the glycine residues in PNA backbone with various chiral amino acids [67][68]. Most of these α

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

• Lei Zhang,
• Greta Linden and
• Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

• -penetrating wavelengths. Peptide nucleic acids (PNAs) [31] are synthetic nucleic acid analogues, in which nucleobases are linked to a repeating N-(2-aminoethyl)glycine polyamide backbone. The lack of phosphate groups provides them with both higher binding affinities to complementary DNA or RNA sequences and

• . Black lines controls: solid: FAM-ssDNA without PNA and under the same conditions; dashed: BHQ/FAM-dsDNA. Solid-phase synthesis of photoswitchable PNAs; Aeg = N-(2-aminoethyl)glycine, Bhoc = benzhydryloxycarbonyl. Isomerization conversions at the photostationary state (PSS). Melting temperatures (TM) of

Synthesis and NMR studies of malonyl-linked glycoconjugates of N-(2-aminoethyl)glycine. Building blocks for the construction of combinatorial glycopeptide libraries

• Markus Nörrlinger,
• Sven Hafner and
• Thomas Ziegler

Beilstein J. Org. Chem. 2016, 12, 1939–1948, doi:10.3762/bjoc.12.183

• determine the coalescence temperature which resulted in calculated rotation barriers of 17.9–18.3 kcal/mol for the rotamers. Keywords: amino acids; carbohydrates; glycoconjugates; glycopeptides; N-(2-aminoethyl)glycine; Introduction The glycocalyx is a fringy or fuzzy polysaccharide layer coating most

• ligand are highly desirable [10][11][12][13]. In our previous work we introduced various trifunctional glycopeptide building blocks derived from aspartic acid, 3-aminomethyl-5-aminobenzoic acid [14] and from the PNA-like N-(2-aminoethyl)glycine (AEG) backbone to which sugar moieties were linked through

Synthesis of aromatic glycoconjugates. Building blocks for the construction of combinatorial glycopeptide libraries

• Markus Nörrlinger and
• Thomas Ziegler

Beilstein J. Org. Chem. 2014, 10, 2453–2460, doi:10.3762/bjoc.10.256

• focus was on glycosylated amino acid building blocks derived from aspartic acid and from the PNA-like N-(2-aminoethyl)glycine (AEG) backbone to which the sugar moieties were attached through either simple alkyl chains [5][6], amino alcohols [7][8] or 1,2,3-triazoles [9][10][11]. These building blocks