Contemporary strategies for peptide macrocyclization

Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides

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Synthesis of Proteins by Native Chemical Ligation

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Amide bond formation and peptide coupling

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The exploration of macrocycles for drug discovery — an underexploited structural class

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Activation of Apoptosis in Vivo by a Hydrocarbon-Stapled BH3 Helix

Walensky, L. D., Kung, A. L., Escher, I., Malia, T. J., Barbuto, S., Wright, R. D., Wagner, G., Verdine, G. L., & Korsmeyer, S. J. (2004) · Science · doi:10.1126/science.1099191 · Cited by 1,349 · see citing works

Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides

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Modern Variants of the Mannich Reaction

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Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides

Zhang, L., Chen, X., Xue, P., Sun, H. H. Y., Williams, I. D., Sharpless, K. B., Fokin, V. V., & Jia, G. (2005) · Journal of the American Chemical Society · doi:10.1021/ja054114s · Cited by 1,124 · see citing works

An All-Hydrocarbon Cross-Linking System for Enhancing the Helicity and Metabolic Stability of Peptides

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Synthesis of Peptides and Proteins without Cysteine Residues by Native Chemical Ligation Combined with Desulfurization

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Highly Efficient Synthesis of Covalently Cross-Linked Peptide Helices by Ring-Closing Metathesis

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Reverse Turns in Peptides and Protein

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Macrolactonizations in the Total Synthesis of Natural Products

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Peptides: Chemistry and Biology

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The cyclization of peptides and depsipeptides

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Application of Ring-Closing Metathesis to the Synthesis of Rigidified Amino Acids and Peptides

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Proteases Universally Recognize Beta Strands In Their Active Sites

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Pseudo-Prolines as a Solubilizing, Structure-Disrupting Protection Technique in Peptide Synthesis

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Nonribosomal Peptide Synthetases Involved in the Production of Medically Relevant Natural Products

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A Heterocyclic Peptide Nanotube

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Gramicidin S and its use in the Treatment of Infected Wounds

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Biomimetic synthesis and optimization of cyclic peptide antibiotics

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1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics

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Reprogramming the Translation Initiation for the Synthesis of Physiologically Stable Cyclic Peptides

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A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides

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Macrocyclization of Linear Peptides Enabled by Amphoteric Molecules

Hili, R., Rai, V., & Yudin, A. K. (2010) · Journal of the American Chemical Society · doi:10.1021/ja910544p · Cited by 233 · see citing works

The synthesis of cyclic peptides

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A Highly Stable Short α-Helix Constrained by a Main-Chain Hydrogen-Bond Surrogate

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Flexible Molecules with Defined Shape—Conformational Design

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Head‐to‐Tail Peptide Cyclodimerization by Copper‐Catalyzed Azide–Alkyne Cycloaddition

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Protein Prosthesis: 1,5-Disubstituted[1,2,3]triazoles as cis-Peptide Bond Surrogates

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Conformation‐Directed Macrocyclization Reactions

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DNA-Directed Functionalization of Colloidal Gold with Proteins This work was supported by Deutsche Forschungsgemeinschaft and Fonds der Chemischen Industrie. We thank Prof. D. Blohm for helpful discussions and generous support.

Niemeyer, C. M., & Ceyhan, B. (2001) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20011001)40:19 · Cited by 197 · see citing works

Click Chemistry as a Route to Cyclic Tetrapeptide Analogues: Synthesis ofcyclo-[Pro-Val-ψ(triazole)-Pro-Tyr]

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Synthesis and Application of Unprotected Cyclic Peptides as Building Blocks for Peptide Dendrimers

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Highly Stable Self-Assembly in Water: Ion Pair Driven Dimerization of a Guanidiniocarbonyl Pyrrole Carboxylate Zwitterion

Schmuck, C., & Wienand, W. (2002) · Journal of the American Chemical Society · doi:10.1021/ja028485+ · Cited by 176 · see citing works

Pseudo-Prolines as a Molecular Hinge: Reversible Induction ofcisAmide Bonds into Peptide Backbones

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Round and Round we Go: Cyclic Peptides in Disease

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Click Chemistry as a Macrocyclization Tool in the Solid-Phase Synthesis of Small Cyclic Peptides

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Cyclization ofall- l -Pentapeptides by Means of 1-Hydroxy-7-azabenzotriazole-Derived Uronium and Phosphonium Reagents

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Efficient Route toC2Symmetric Heterocyclic Backbone Modified Cyclic Peptides

van Maarseveen, J. H., Horne, W. S., & Ghadiri, M. R. (2005) · Organic Letters · doi:10.1021/ol0518028 · Cited by 153 · see citing works

Evaluation of Biologically Relevant Short α-Helices Stabilized by a Main-Chain Hydrogen-Bond Surrogate

Wang, D., Chen, K., Kulp, J. L., & Arora, P. S. (2006) · Journal of the American Chemical Society · doi:10.1021/ja062710w · Cited by 152 · see citing works

Probing the Bioactive Conformation of an Archetypal Natural Product HDAC Inhibitor with Conformationally Homogeneous Triazole‐Modified Cyclic Tetrapeptides

Horne, W. S., Olsen, C. A., Beierle, J. M., Montero, A., & Ghadiri, M. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200805900 · Cited by 152 · see citing works

Translation of DNA into a Library of 13 000 Synthetic Small-Molecule Macrocycles Suitable for in Vitro Selection

Tse, B. N., Snyder, T. M., Shen, Y., & Liu, D. R. (2008) · Journal of the American Chemical Society · doi:10.1021/ja805649f · Cited by 147 · see citing works

Applications of BOP reagent in solid phase synthesis

Felix, A. M., Wang, C., Heimer, E. P., & Fournier, A. (1988) · International journal of peptide & protein research · doi:10.1111/j.1399-3011.1988.tb00028.x · Cited by 142 · see citing works

Thia Zip Reaction for Synthesis of Large Cyclic Peptides: Mechanisms and Applications

Tam, J. P., Lu, Y., & Yu, Q. (1999) · Journal of the American Chemical Society · doi:10.1021/ja984480u · Cited by 142 · see citing works

Practical synthesis of cyclic peptides, with an example of dependence of cyclization yield upon linear sequence

Brady, S. F., Varga, S. L., Freidinger, R. M., et al. (1979) · The Journal of Organic Chemistry · doi:10.1021/jo01332a003 · Cited by 139 · see citing works

Chemistry of polymer-bound o-benzyne. Frequency of encounter between substituents on crosslinked polystyrenes

Mazur, S., & Jayalekshmy, P. (1979) · Journal of the American Chemical Society · doi:10.1021/ja00497a032 · Cited by 136 · see citing works

Cyclic RGD Peptides Containing β-Turn Mimetics

Haubner, R., Schmitt, W., Hölzemann, G., Goodman, S. L., Jonczyk, A., & Kessler, H. (1996) · Journal of the American Chemical Society · doi:10.1021/ja9608757 · Cited by 135 · see citing works

Some ‘difficult sequences’ made easy

Hyde, C. B., Johnson, T., OWEN, D., et al. (1994) · International journal of peptide & protein research · doi:10.1111/j.1399-3011.1994.tb00541.x · Cited by 135 · see citing works

Cyclotetrapeptides and cyclopentapeptides: occurrence and synthesis*

Schmidt, U., & Langner, J. (1997) · Journal of Peptide Research · doi:10.1111/j.1399-3011.1997.tb01122.x · Cited by 126 · see citing works

Some 'difficult sequences' made easy. A study of interchain association in solid-phase peptide synthesis.

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High-Throughput Sequence Determination of Cyclic Peptide Library Members by Partial Edman Degradation/Mass Spectrometry

Joo, S. H., Xiao, Q., Ling, Y. L., et al. (2006) · Journal of the American Chemical Society · doi:10.1021/ja063722k · Cited by 117 · see citing works

Design and Synthesis of Cyclic RGD Pentapeptoids by Consecutive Ugi Reactions

Vercillo, O. E., Andrade, C. K. Z., & Wessjohann, L. A. (2007) · Organic Letters · doi:10.1021/ol702521g · Cited by 117 · see citing works

Cyclic Peptides from Linear Unprotected Peptide Precursors through Thiazolidine Formation

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Conformational Analysis of Reverse-Turn Constraints by N-Methylation and N-Hydroxylation of Amide Bonds in Peptides and Non-Peptide Mimetics

Takeuchi, Y., & Marshall, G. R. (1998) · Journal of the American Chemical Society · doi:10.1021/ja970855k · Cited by 114 · see citing works

Structural Mimicry of Canonical Conformations in Antibody Hypervariable Loops Using Cyclic Peptides Containing a Heterochiral Diproline Template

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N-Methylated Cyclic Pentaalanine Peptides as Template Structures

Chatterjee, J., Mierke, D. F., & Kessler, H. (2006) · Journal of the American Chemical Society · doi:10.1021/ja063123d · Cited by 112 · see citing works

Chemoselective Peptide Cyclization by Traceless Staudinger Ligation

Kleineweischede, R., & Hackenberger, C. P. R. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200801514 · Cited by 112 · see citing works

Synchronized Synthesis of Peptide‐Based Macrocycles by Digital Microfluidics

Jebrail, M. J., Ng, A. H. C., Rai, V., Hili, R., Yudin, A. K., & Wheeler, A. R. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201001604 · Cited by 109 · see citing works

Invited reviewnative chemical ligation applied to the synthesis and bioengineering of circular peptides and proteins

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Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions

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Chemoselective backbone cyclization of unprotected peptides

Camarero, J. A., & Muir, T. W. (1997) · Chemical Communications · doi:10.1039/a702083j · Cited by 100 · see citing works

On-resin peptide macrocyclization using thiol–ene click chemistry

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An improved method for the solution cyclization of peptides under pseudo-high dilution conditions

Malešević, M., Strijowski, U., Bächle, D., et al. (2004) · Journal of Biotechnology · doi:10.1016/j.jbiotec.2004.03.015 · Cited by 99 · see citing works

1,3-Dipolar Cycloadditions

Merino, P. (2004) · Heteroatom Analogues of Aldehydes and Ketones · doi:10.1055/sos-sd-027-00467 · Cited by 98 · see citing works

Conformationally Homogeneous Heterocyclic Pseudotetrapeptides as Three‐Dimensional Scaffolds for Rational Drug Design: Receptor‐Selective Somatostatin Analogues

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Via Ugi reactions to conformationally fixed cyclic peptidesDedicated to Professor Dr D. Seebach on the occasion of his 65th birthday.

Hebach, C., & Kazmaier, U. (2003) · Chemical Communications · doi:10.1039/b210952b · Cited by 95 · see citing works

A novel method to synthesize cyclic peptides

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Solubilization of Peptides in Non‐polar Organic Solvents by the Addition of Inorganic Salts: Facts and Implications

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Pseudoprolines as Removable Turn Inducers: Tools for the Cyclization of Small Peptides

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Lactone and Lactam Library Synthesis by Silver Ion-Assisted Orthogonal Cyclization of Unprotected Peptides

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Synthesis of Difficult Cyclic Peptides by Inclusion of a Novel Photolabile Auxiliary in a Ring Contraction Strategy

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Prediction of the best linear precursor in the synthesis of cyclotetrapeptides by molecular mechanic calculations

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Difficult Macrocyclizations: New Strategies for Synthesizing Highly Strained Cyclic Tetrapeptides

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New segment-coupling method for peptide synthesis in aqueous solution: application to synthesis of human [Gly17]-beta-endorphin.

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On-Resin Native Chemical Ligation for Cyclic Peptide Synthesis 1 , 2

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On‐resin head‐to‐tail cyclization of cyclotetrapeptides: optimization of crucial parameters

Alcaro, M. C., Sabatino, G., Uziel, J., Chelli, M., Ginanneschi, M., Rovero, P., & Papini, A. M. (2003) · Journal of Peptide Science · doi:10.1002/psc.512 · Cited by 73 · see citing works

Conformational Control by Thiazole and Oxazoline Rings in Cyclic Octapeptides of Marine Origin. Novel Macrocyclic Chair and Boat Conformations

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Conformational Preferences of Short Peptide Fragments

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Organic chemistry on the solid phase. Site-site interactions on functionalized polystyrene

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Recent Progress of Synthetic Studies to Peptide and Peptidomimetic Cyclization

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Ruthenium‐Catalyzed Cycloaddition of Alkynes and Organic Azides.

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Synthesis of All- l Cyclic Tetrapeptides Using Pseudoprolines as Removable Turn Inducers

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Conformational Preference and Potential Templates of N‐Methylated Cyclic Pentaalanine Peptides

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Kinetic Control of Proline Amide Rotamers: Total Synthesis of trans,trans- and cis,cis-Ceratospongamide

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Synthesis of cyclic peptides via O–N-acyl migration

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Cyclative Cleavage through Dipolar Cycloaddition: Polymer‐Bound Azidopeptidylphosphoranes Deliver Locked cis‐ Triazolylcyclopeptides as Privileged Protein Binders

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Hydrogen-Bond Driven Loop-Closure Kinetics in Unfolded Polypeptide Chains

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A New Tri-Orthogonal Strategy for Peptide Cyclization

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Synthesis of Cyclic Peptides through Direct Aminolysis of Peptide Thioesters Catalyzed by Imidazole in Aqueous Organic Solutions

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Metal ion-assisted peptide cyclization

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ChemInform Abstract: Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides

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Photolithographic synthesis of cyclic peptide arrays using a differential deprotection strategy

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Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification

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Cyclic hexapeptides derived from the human thymopoietin III

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Peptides—XIII

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Pseudo-prolines in cyclic peptides: Conformational stabilisation of cyclo[Pro-Thr(ψMe,Mepro)-Pro]

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Metathesis assisted synthesis of cyclic peptides

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Efficient parallel synthesis of macrocyclic peptidomimetics

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Modeling of peptides containing D-amino acids: implications on cyclization

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A pincer auxiliary to force difficult lactamisations

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Cyclization of several linear penta‐ and heptapeptides with different metal ions studied by CD spectroscopy*

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Cyclic Peptide Synthesis with Thioacids

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