Peptidomimetics via copper-catalyzed azide–alkyne cycloadditions

Angell, Yu; Burgess, Kevin

doi:10.1039/b701444a

Cited by 546 publications

(280 citation statements)

References 68 publications

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“…[36,37] Reviews also describe applications in synthesis of peptidomimetics, [38,39] in bioconjugations [40][41][42] and surface chemistry. [43] It has been compared to the Staudinger ligation [37] and used in profiling of proteases [44] and in combinatorial drug discovery.…”

Section: Reviews On Click Chemistrymentioning

confidence: 99%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,155

508

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The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of click chemistry due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.

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Section: Reviews On Click Chemistrymentioning

confidence: 99%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,155

508

View full text Add to dashboard Cite

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“…Indolizidine-2-one and -9-one amino acids, representing 6,5 and 5,6 scaffolds, were used as β-turn scans to explore the conformational requirements for activity of analogues of Calcitonin-gene related peptide (CGRP) antagonist, together with aza-aminoacid scans [32]. The importance of a type II' β-turn centered at Gly 33 [27][28][29][30][31][32][33][34][35][36][37] has been illustrated by increased antagonistic potency of the azaGly 33 and indolizidine-2-one amino acid [33][34] analogues. In addition, the improved metabolic stability and longer duration of action qualifies those scans to be another peptidomimetic research tool.…”

Section: Conformationally Restricted β-Turn Dipeptide Mimeticsmentioning

confidence: 99%

Peptidomimetics, a synthetic tool of drug discovery

Vagner

Hruby

2008

Current Opinion in Chemical Biology

469

302

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SummaryThe demand for modified peptides with improved stability profiles and pharmacokinetic properties is driving extensive research effort in this field. Many structural modifications of peptides guided by rational design and molecular modeling have been established to develop novel synthetic approaches. Recent advances in the synthesis of conformationally restricted building blocks and peptide bond isosteres are discussed.

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“…1,2 The observed CT in natural proteins 3 led researchers to synthesize a number of artificial analogues that can mimic one or more functions of their natural counterparts. 4,5 These synthetic analogues are called peptidomimetics and are potentially used in catalysis, biosensors, electronic devices, and drug synthesis on the basis of their conducting and CT natures. 6,7 Peptidomimetics and their applications have been extensively studied using various experimental and theoretical methods.…”

Section: ■ Introductionmentioning

confidence: 99%

Computational Studies on Structural, Excitation, and Charge-Transfer Properties of Ureidopeptidomimetics

2016

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Peptides with ureido group enclosing backbones are considered peptidomimetics and are known for their higher stabilities, biocompatibilities, antibiotic, inhibitor, and charge-transduction activities. These peptidomimetics have some unique applications, which are quite different from those of natural peptides. Hence, it is imperative to appreciate their properties at a microscopic level. In this regard, this work outlines, in detail, the charge transfer (CT) properties, holemigration dynamics, and electronic structures of various experimentally comprehended ureidopeptidomimetic models using density functional theory (DFT). Time-dependent DFT and complete active space self-consistent field computations on basic models provide the necessary evidence for the viability of CT from the end enfolding the ureido group to the other end with a carboxylate entity. This donor-to-acceptor CT has been reflected in excitation studies, in which the higher intensity band corresponds to CT from the π orbital of the ureido group to the π* orbital of the carboxylate entity. Further, hole-migration studies have shown that charge can evolve from the ureido end, whereas the hole generated at the carboxylate end does not migrate. However, hole migration has been reported to occur from both ends (amino and carboxylate ends) in glycine oligopeptides, and our studies show that the ability to transfer and migrate charge can be tuned by modifying the donor and acceptor functional groups in both the neutral and cationic charge states. We have analyzed the possibility of hole migration following ionization using DFT-based wave-packet propagation and found its occurrence on a ∼2−5 fs time scale, which reflects the charge-transduction ability of peptidomimetics.

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Peptidomimetics via copper-catalyzed azide–alkyne cycloadditions

Cited by 546 publications

References 68 publications

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Peptidomimetics, a synthetic tool of drug discovery

Computational Studies on Structural, Excitation, and Charge-Transfer Properties of Ureidopeptidomimetics

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