Walking through the wonder years of artificial DNA: peptide nucleic acid

Peptides have been extensively utilized to construct nanomaterials that display targeted structure through hierarchical assembly. The self-assembly of both rationally designed peptides derived from naturally occurring domains in proteins as well as intuitively or computationally designed peptides that form β-sheets and helical secondary structures have been widely successful in constructing nanoscale morphologies with well-defined 1-d, 2-d, and 3-d architectures. In this review, we discuss these successes of peptide self-assembly, especially in the context of designing hierarchical materials. In particular, we emphasize the differences in the level of peptide design as an indicator of complexity within the targeted self-assembled materials and highlight future avenues for scientific and technological advances in this field.

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“…The resulting artificial nucleic acids show good base binding specificity, strength, and helicity. 53…”

Section: Comparisons Of Self-assembling Buildingmentioning

confidence: 99%

Peptide Design and Self-assembly into Targeted Nanostructure and Functional Materials

et al. 2021

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“…[2][3][4] These form stable hybrids with naturally occurring nucleic acid sequences and targets (e.g., duplexes, triplexes, G-quadraplexes, i-motifs, and aptamers), [2,[5][6][7] and unlike classical oligonucleotides, cannot be degraded by nucleases. [8] In recent years, other strategies for connecting nucleobases to peptides have emerged, such as uniting the N1 (pyrimidine) or N9 (purine) nitrogen atoms of one or more nucleobases with alanine-based amino acids through sp 3 CÀ N bonds, referred to as aza-nucleopeptides (aNPs). [9] These structures conserve the amide backbone of peptides enabling them to self-assemble and to recognize target oligonucleotides in ways akin to standard peptides.…”

Section: Introductionmentioning

confidence: 99%

carba‐Nucleopeptides (cNPs): A Biopharmaceutical Modality Formed through Aqueous Rhodamine B Photoredox Catalysis

Immel

Bloom

2022

Angewandte Chemie

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Exchanging the ribose backbone of an oligonucleotide for a peptide can enhance its physiologic stability and nucleic acid binding affinity. Ordinarily, the eneamino nitrogen atom of a nucleobase is fused to the side chain of a polypeptide through a new CÀ N bond. The discovery of CÀ C linked nucleobases in the human transcriptome reveals new opportunities for engineering nucleopeptides that replace the traditional CÀ N bond with a non-classical CÀ C bond, liberating a captive nitrogen atom and promoting new hydrogen bonding and π-stacking interactions. We report the first late-stage synthesis of CÀ C linked carba-nucleopeptides (cNPs) using aqueous Rhodamine B photoredox catalysis. We prepare brand-new cNPs in batch, in parallel, and in flow using three long-wavelength photochemical setups. We detail the mechanism of our reaction by experimental and computational studies and highlight the essential role of diisopropylethylamine as a bifurcated twoelectron reductant.

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“…14 Moreover, the enzyme-activated intracellular colloidal formation can also act as a "nanoreactor" to facilitate in situ drug release and overcome the obstacle of inefficient dosing due to the relatively low concentration of drug uptake. 15 Recently, nucleic bases have been introduced as new functional building blocks into the PAs, 16 due to their diverse stimuli-responsiveness (e.g., high affinity with oligonucleotides, 17 multiple hydrogen bonding in duplexes/triplexes, 18 metal ion coordination, 19 pH/photo-responsiveness 20 ) as well as good biocompatibility and biodegradability. 21 The design and fabrication of nucleic based tethered PAs are thus enriched.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, nucleic bases have been introduced as new functional building blocks into the PAs, 16 due to their diverse stimuli-responsiveness ( e.g. , high affinity with oligonucleotides, 17 multiple hydrogen bonding in duplexes/triplexes, 18 metal ion coordination, 19 pH/photo-responsiveness 20 ) as well as good biocompatibility and biodegradability.…”

Section: Introductionmentioning

confidence: 99%

A crosslinked colloidal network of peptide/nucleic base amphiphiles for targeted cancer cell encapsulation

et al. 2021

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Walking through the wonder years of artificial DNA: peptide nucleic acid

Cited by 10 publications

References 93 publications

Peptide Design and Self-assembly into Targeted Nanostructure and Functional Materials

Peptide Design and Self-assembly into Targeted Nanostructure and Functional Materials

carba‐Nucleopeptides (cNPs): A Biopharmaceutical Modality Formed through Aqueous Rhodamine B Photoredox Catalysis

A crosslinked colloidal network of peptide/nucleic base amphiphiles for targeted cancer cell encapsulation

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