Nitrilium ion trapping as a strategy to access structurally diverse heterobiaryl-containing peptide macrocycles

Yudin, Andrei K.; Diamandas, Matthew; Heller, Nicholas

doi:10.1039/d3sc03058j

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2024

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Cited by 3 publications

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Chemical cyclization of tyrosine-containing peptides via in situ generated triazolinedione peptides

Keyes,

Mifflin,

Austin

et al. 2024

Peptide and Peptide Mimicking Tools: Methods, Synthesis, Design &Amp; Applications

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Chemical cyclization of tyrosine-containing peptides via in situ generated triazolinedione peptides

Keyes,

Mifflin,

Austin

et al. 2024

Peptide and Peptide Mimicking Tools: Methods, Synthesis, Design &Amp; Applications

View full text Add to dashboard Cite

Stabilization of 3₁₀-Helices in Macrocycles Using Dominant Rotor Methodology

Širvinskas,

Saunders,

Mitrache

et al. 2024

J. Am. Chem. Soc.

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Stabilization of biologically relevant structural motifs has been a long-standing challenge. Here we show that atropisomeric dominant rotors can stabilize rare 3 10 -helices in macrocycles. The target molecules were prepared using solid-phase peptide synthesis and subjected to extensive structural analysis. Molecular dynamics (MD) simulations enabled us to acquire solution structures for the target molecules, which offered evidence for stable 3 10 -helix formation, ordinarily a metastable state. The 3 10 -helices were shown to retain helicity after heating to 100 °C for 72 h. Moreover, the crude atropisomeric mixtures could be thermally enriched toward 3 10 -helical macrocycles with selectivities of >20:1.

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Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade

Ye,

Pan,

Huang

et al. 2024

Chem. Sci.

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Nitrilium ion trapping as a strategy to access structurally diverse heterobiaryl-containing peptide macrocycles

Abstract: Biaryl and heterobiaryl-containing cyclic peptides represent promising scaffolds for the development of bioactive molecules. The incorporation of heterobiaryl motifs continues to pose synthetic challenges, which is partially due to the...

Cited by 3 publications

References 17 publications

Chemical cyclization of tyrosine-containing peptides via in situ generated triazolinedione peptides

Chemical cyclization of tyrosine-containing peptides via in situ generated triazolinedione peptides

Stabilization of 3₁₀-Helices in Macrocycles Using Dominant Rotor Methodology

Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade

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Nitrilium ion trapping as a strategy to access structurally diverse heterobiaryl-containing peptide macrocycles

Abstract: Biaryl and heterobiaryl-containing cyclic peptides represent promising scaffolds for the development of bioactive molecules. The incorporation of heterobiaryl motifs continues to pose synthetic challenges, which is partially due to the...

Cited by 3 publications

References 17 publications

Chemical cyclization of tyrosine-containing peptides via in situ generated triazolinedione peptides

Chemical cyclization of tyrosine-containing peptides via in situ generated triazolinedione peptides

Stabilization of 310-Helices in Macrocycles Using Dominant Rotor Methodology

Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade

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Product

Resources

About

Stabilization of 3₁₀-Helices in Macrocycles Using Dominant Rotor Methodology