Postsynthetic modification of peptoids via the <scp>S</scp>uzuki‐<scp>M</scp>iyaura cross‐coupling reaction

Nam, Ho Yeon; Seo, Jiwon

doi:10.1002/bip.22747

Cited by 10 publications

(9 citation statements)

References 39 publications

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“…This bisignate ECCD signal splitting, a hallmark of structured molecules, was observed in all solution conditions, and provided further evidence that the naphthalenes in 1 were in an ordered, chiral environment. Flexible polymers functionalized with naphthalene or pyrene aromatic side chains, including unstructured peptoids, do not show induced CD signals in this region …”

Section: Resultsmentioning

confidence: 93%

Solution effects on the self‐association of a water‐soluble peptoid

et al. 2018

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A desire to replicate the structural and functional complexity of proteins with structured, sequence‐specific oligomers motivates study of the structural features of water‐soluble peptoids (N‐substituted glycine oligomers). Understanding the molecular‐level details of peptoid self‐assembly in water is essential to advance peptoids' application as novel materials. Peptoid 1, an amphiphilic, putatively helical peptoid previously studied in our laboratory, shows evidence of self‐association in aqueous solution. In this work, we evaluate how changes to aqueous solution conditions influence the self‐association of 1. We report that changes to pH influence the fluorescence and CD spectroscopic features as well as the peptoid's interaction with a solvatochromic fluorophore and its apparent size as estimated by size exclusion chromatography. Addition of guanidine hydrochloride and ammonium sulfate also modulate spectroscopic features of the peptoid, its interaction with a solvatochromic fluorophore, and its elution in size exclusion chromatography. These data suggest that the ordering of the self‐assembly changes in response to pH and with solvent additives and is more ordered at higher pH and in the presence of guanidine hydrochloride. The deeper understanding of the self‐association of 1 afforded by these studies informs the design of new stimuli‐responsive peptoids with stable tertiary or quaternary structures.

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Section: Resultsmentioning

confidence: 93%

Solution effects on the self‐association of a water‐soluble peptoid

et al. 2018

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“…Another work, using peptoids as substrates, describes a solid‐phase biaryl synthesis for the generation of linear peptidomimetics analogues of the Smac protein, displaying hydrophobic pharmacophore elements [45] . Different biaryl peptoids were obtained through this strategy, which exhibits potential application in material sciences [46] …”

Section: Classical Pd‐catalyzed Reactions In Solid Phasementioning

confidence: 99%

Transition Metal‐Catalyzed Reactions and Solid‐Phase Synthesis: A Convenient Blend

et al. 2022

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Transition metal‐catalyzed, C−C and C−N bond‐forming reactions have made an enormous impact in the way complex molecules are assembled. The benefits of solid‐phase chemistry soon made this type of reaction applicable to solid‐supported processes. In this review, we report the most recent applications and possibilities of this combination. Remarkably, the solid‐phase CuAAC and ring‐closing metathesis have demonstrated an important role in synthetic biology, alike more traditional Pd‐catalyzed reactions, such as Suzuki‐Miyaura, Heck, Sonogashira, which are valuable tools for accessing libraries of biologically relevant small molecules. Examples proved the validity of solid‐phase transition metal‐catalyzed reactions as a practical and fast strategy to cover the current organic chemistry demands.

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“…7 Interestingly, the SM coupling sequence in the presence of an aqueous palladium ligand system has been employed for the installation of 18 F into a protein, thus providing an efficient protocol toward 18 F-labeled peptides or proteins. 8 Recently, a SM coupling has also been used in an efficient manner for post-synthetic side-chain modification of peptoids 9 and biaryl-linked cyclic peptoids on a solid-phase resin. 10 It should be noted that olefin metathesis is one of the most versatile methods for carbon-carbon bond formation and this strategy has been used in efficient chemical modifications of peptides.…”

Section: Introductionmentioning

confidence: 99%

Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions

Kotha

Meshram²,

Panguluri³

2019

Synthesis

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We have summarized diverse synthetic approaches for the modification of peptides by employing transition-metal-catalyzed reactions. These methods can deliver unusual peptides suitable for peptidomimetics. To this end, several popular reactions such as Diels–Alder, 1,3-dipolar cycloaddition, [2+2+2] cyclotrimerization, metathesis, Suzuki–Miyaura cross-coupling, and Negishi coupling have been used to assemble modified peptides by post-assembly chemical modification strategies.1 Introduction2 Synthesis of a Cyclic α-Amino Acid Derivative via a Ring-Closing Metathesis Protocol3 Peptide Modification Using a Ring-Closing Metathesis Strategy4 Peptide Modification via a [2+2+2] Cyclotrimerization Reaction5 Peptide Modification by Using [2+2+2] Cyclotrimerization and Suzuki Coupling6 Peptide Modification via a Suzuki–Miyaura Cross-Coupling7 Peptide Modification via Cross-Enyne Metathesis and a Diels–Alder Reaction as Key Steps8 Peptide Modification via 1,3-Dipolar Cycloaddition Reactions9 Modified Peptides via Negishi Coupling10 A Modified Dipeptide via Ethyl Isocyanoacetate11 Conclusions

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Postsynthetic modification of peptoids via the Suzuki‐Miyaura cross‐coupling reaction

Cited by 10 publications

References 39 publications

Solution effects on the self‐association of a water‐soluble peptoid

Solution effects on the self‐association of a water‐soluble peptoid

Transition Metal‐Catalyzed Reactions and Solid‐Phase Synthesis: A Convenient Blend

Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions

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