Contemporary strategies for peptide macrocyclization.

[1]  A. Wheeler,et al.  Synchronized synthesis of peptide-based macrocycles by digital microfluidics. , 2010, Angewandte Chemie.

[2]  David J Craik,et al.  Native chemical ligation applied to the synthesis and bioengineering of circular peptides and proteins. , 2010, Biopolymers.

[3]  Jörg Rademann,et al.  Cyclative cleavage through dipolar cycloaddition: polymer-bound azidopeptidylphosphoranes deliver locked cis-triazolylcyclopeptides as privileged protein binders. , 2010, Angewandte Chemie.

[4]  K. Jolliffe,et al.  Synthesis of all-L cyclic tetrapeptides using pseudoprolines as removable turn inducers. , 2010, Organic letters.

[5]  D. Crich,et al.  Cyclic peptide synthesis with thioacids. , 2010, Organic letters.

[6]  K. Anseth,et al.  On-resin peptide macrocyclization using thiol-ene click chemistry. , 2010, Chemical communications.

[7]  R. Houghten,et al.  Macrolactonization of peptide thioesters catalyzed by imidazole and its application in the synthesis of kahalalide B and analogues. , 2010, Organic letters.

[8]  S. Danishefsky,et al.  Total synthesis of cyclosporine: access to N-methylated peptides via isonitrile coupling reactions. , 2010, Journal of the American Chemical Society.

[9]  Vishal Rai,et al.  Macrocyclization of linear peptides enabled by amphoteric molecules. , 2010, Journal of the American Chemical Society.

[10]  Jeremy C. Smith,et al.  Hydrogen-Bond Driven Loop-Closure Kinetics in Unfolded Polypeptide Chains , 2010, PLoS Comput. Biol..

[11]  M. Fujita,et al.  Conformational preferences of short peptide fragments. , 2009, Angewandte Chemie.

[12]  Austin B. Yongye,et al.  Synthesis of cyclic peptides through direct aminolysis of peptide thioesters catalyzed by imidazole in aqueous organic solutions. , 2009, Journal of combinatorial chemistry.

[13]  Austin B. Yongye,et al.  Modeling of peptides containing D-amino acids: implications on cyclization , 2009, J. Comput. Aided Mol. Des..

[14]  M Reza Ghadiri,et al.  Probing the bioactive conformation of an archetypal natural product HDAC inhibitor with conformationally homogeneous triazole-modified cyclic tetrapeptides. , 2009, Angewandte Chemie.

[15]  John M. Beierle,et al.  Conformationally homogeneous heterocyclic pseudotetrapeptides as three-dimensional scaffolds for rational drug design: receptor-selective somatostatin analogues. , 2009, Angewandte Chemie.

[16]  Jomana Elaridi,et al.  Metathesis assisted synthesis of cyclic peptides. , 2009, Chemical communications.

[17]  A. Fournier,et al.  Applications of BOP reagent in solid phase synthesis. II: Solid phase side-chain to side-chain cyclizations using BOP reagent , 2009 .

[18]  U. Schmidt,et al.  Cyclotetrapeptides and cyclopentapeptides: occurrence and synthesis. , 2009, The journal of peptide research : official journal of the American Peptide Society.

[19]  R. Sheppard,et al.  Some 'difficult sequences' made easy. A study of interchain association in solid-phase peptide synthesis. , 2009, International journal of peptide and protein research.

[20]  H. Kessler,et al.  Cyclic hexapeptides derived from the human thymopoietin III. , 2009, International journal of peptide and protein research.

[21]  K. Fan,et al.  Cyclization of several linear penta- and heptapeptides with different metal ions studied by CD spectroscopy. , 2008, The journal of peptide research : official journal of the American Peptide Society.

[22]  David R. Liu,et al.  Translation of DNA into a library of 13,000 synthetic small-molecule macrocycles suitable for in vitro selection. , 2008, Journal of the American Chemical Society.

[23]  D. Tai,et al.  Molecularly imprinted cavities template the macrocyclization of tetrapeptides. , 2008, Chemical communications.

[24]  P. Roller,et al.  Recent Progress of Synthetic Studies to Peptide and Peptidomimetic Cyclization , 2008 .

[25]  Daniel Fortin,et al.  Efficient parallel synthesis of macrocyclic peptidomimetics. , 2008, Bioorganic & medicinal chemistry letters.

[26]  Jean Martínez,et al.  Synthesis of cyclic peptides via O–N-acyl migration , 2008 .

[27]  C. Hackenberger,et al.  Chemoselective peptide cyclization by traceless Staudinger ligation. , 2008, Angewandte Chemie.

[28]  Stephen P. Hale,et al.  The exploration of macrocycles for drug discovery — an underexploited structural class , 2008, Nature Reviews Drug Discovery.

[29]  Douglas A. Horton,et al.  Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification. , 2008, Organic & biomolecular chemistry.

[30]  H. Kessler,et al.  Conformational preference and potential templates of N-methylated cyclic pentaalanine peptides. , 2008, Chemistry.

[31]  Michael G Thomas,et al.  Nonribosomal peptide synthetases involved in the production of medically relevant natural products. , 2008, Molecular pharmaceutics.

[32]  H. Murakami,et al.  Reprogramming the translation initiation for the synthesis of physiologically stable cyclic peptides. , 2008, ACS chemical biology.

[33]  C. K. Andrade,et al.  Design and synthesis of cyclic RGD pentapeptoids by consecutive Ugi reactions. , 2008, Organic letters.

[34]  R. Raines,et al.  Protein prosthesis: 1,5-disubstituted[1,2,3]triazoles as cis-peptide bond surrogates. , 2007, Journal of the American Chemical Society.

[35]  R. Lokey,et al.  Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides. , 2007, Organic letters.

[36]  D. Speijer,et al.  1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics. , 2007, Organic & biomolecular chemistry.

[37]  Theodore V. Tselios,et al.  Cyclic Peptides in Disease , 2007 .

[38]  H. Kessler,et al.  N-methylated cyclic pentaalanine peptides as template structures. , 2006, Journal of the American Chemical Society.

[39]  S. Joo,et al.  High-throughput sequence determination of cyclic peptide library members by partial Edman degradation/mass spectrometry. , 2006, Journal of the American Chemical Society.

[40]  Vasso Apostolopoulos,et al.  Round and round we go: cyclic peptides in disease. , 2006, Current medicinal chemistry.

[41]  Kang Chen,et al.  Evaluation of biologically relevant short alpha-helices stabilized by a main-chain hydrogen-bond surrogate. , 2006, Journal of the American Chemical Society.

[42]  Ian D. Williams,et al.  Ruthenium-catalyzed cycloaddition of alkynes and organic azides. , 2006, Journal of the American Chemical Society.

[43]  J. Reek,et al.  Carbosilane dendrimeric carbodiimides: site isolation as a lactamization tool. , 2006, The Journal of organic chemistry.

[44]  J. V. van Maarseveen,et al.  Click chemistry as a route to cyclic tetrapeptide analogues: synthesis of cyclo-[Pro-Val-psi(triazole)-Pro-Tyr]. , 2006, Organic letters.

[45]  J. Campagne,et al.  Macrolactonizations in the total synthesis of natural products. , 2006, Chemical reviews.

[46]  C. Montalbetti,et al.  Amide bond formation and peptide coupling , 2005 .

[47]  M. Ghadiri,et al.  Efficient route to C2 symmetric heterocyclic backbone modified cyclic peptides. , 2005, Organic letters.

[48]  Jieping Zhu,et al.  Conformation-directed macrocyclization reactions , 2005 .

[49]  M. Finn,et al.  Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition. , 2005, Angewandte Chemie.

[50]  D. Fairlie,et al.  Proteases universally recognize beta strands in their active sites. , 2005, Chemical reviews.

[51]  Nishanth Marthandan,et al.  Photolithographic synthesis of cyclic peptide arrays using a differential deprotection strategy. , 2005, Chemical communications.

[52]  K. Jolliffe,et al.  Pseudoprolines as removable turn inducers: tools for the cyclization of small peptides. , 2004, The Journal of organic chemistry.

[53]  Paramjit S. Arora,et al.  A highly stable short α-helix constrained by a main-chain hydrogen-bond surrogate , 2004 .

[54]  S. Korsmeyer,et al.  Activation of Apoptosis in Vivo by a Hydrocarbon-Stapled BH3 Helix , 2004, Science.

[55]  N. Sewald,et al.  An improved method for the solution cyclization of peptides under pseudo-high dilution conditions. , 2004, Journal of biotechnology.

[56]  Judit Tulla-Puche,et al.  On-resin native chemical ligation for cyclic peptide synthesis. , 2004, The Journal of organic chemistry.

[57]  M. Chelli,et al.  On‐resin head‐to‐tail cyclization of cyclotetrapeptides: optimization of crucial parameters , 2004, Journal of peptide science : an official publication of the European Peptide Society.

[58]  G. Tian,et al.  Studies on the Synthetic Methodology of Head to Tail Cyclization of Linear Peptides , 2003, Letters in Peptide Science.

[59]  Y. Ye,et al.  Studies on the synthetic methodology of head to tail cyclization of linear peptides , 2003, Letters in Peptide Science.

[60]  J. Davies The cyclization of peptides and depsipeptides , 2003, Journal of peptide science : an official publication of the European Peptide Society.

[61]  M Reza Ghadiri,et al.  A heterocyclic peptide nanotube. , 2003, Journal of the American Chemical Society.

[62]  Douglas A. Horton,et al.  Difficult macrocyclizations: new strategies for synthesizing highly strained cyclic tetrapeptides. , 2003, Organic letters.

[63]  H. Schoemaker,et al.  A pincer auxiliary to force difficult lactamisations. , 2003, Organic & biomolecular chemistry.

[64]  U. Kazmaier,et al.  Via Ugi reactions to conformationally fixed cyclic peptides. , 2003, Chemical communications.

[65]  C. Schmuck,et al.  Highly stable self-assembly in water: ion pair driven dimerization of a guanidiniocarbonyl pyrrole carboxylate zwitterion. , 2003, Journal of the American Chemical Society.

[66]  Lu Th,et al.  A New Tri-Orthogonal Strategy for Peptide Cyclization , 2002 .

[67]  Michael D. Burkart,et al.  Biomimetic synthesis and optimization of cyclic peptide antibiotics , 2002, Nature.

[68]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[69]  N. Sewald,et al.  Peptides: Chemistry and Biology , 2002 .

[70]  Morten Meldal,et al.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. , 2002, The Journal of organic chemistry.

[71]  J. Taunton,et al.  Kinetic control of proline amide rotamers: total synthesis of trans,trans- and cis,cis-ceratospongamide. , 2002, Journal of the American Chemical Society.

[72]  P. Dawson,et al.  Design and Synthesis of a Protein Catenane , 2001 .

[73]  P. Dawson,et al.  Design and Synthesis of a Protein Catenane This work was supported by The Skaggs Institute for Chemical Biology, The Sloan Foundation, and NIH-GM570132 (PED). We thank Dr. Songpong Deechongkit for assistance with the analytical ultracentrifuge and CD measurements. , 2001, Angewandte Chemie.

[74]  P. Dawson,et al.  Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization. , 2001, Journal of the American Chemical Society.

[75]  F. Robey Selective and facile cyclization of N-chloroacetylated peptides from the C4 domain of HIV Gp120 in LiCl/DMF solvent systems. , 2000, The journal of peptide research : official journal of the American Peptide Society.

[76]  G. Verdine,et al.  An All-Hydrocarbon Cross-Linking System for Enhancing the Helicity and Metabolic Stability of Peptides , 2000 .

[77]  W. Meutermans,et al.  Synthesis of Difficult Cyclic Peptides by Inclusion of a Novel Photolabile Auxiliary in a Ring Contraction Strategy , 1999 .

[78]  M. Mutter,et al.  Pseudo-prolines in cyclic peptides: Conformational stabilisation of cyclo[Pro-Thr(ψMe,Mepro)-Pro] , 1999 .

[79]  J. Tam,et al.  THIA ZIP REACTION FOR SYNTHESIS OF LARGE CYCLIC PEPTIDES : MECHANISMS AND APPLICATIONS , 1999 .

[80]  J. Tam,et al.  Lactone and Lactam Library Synthesis by Silver Ion-Assisted Orthogonal Cyclization of Unprotected Peptides† , 1999 .

[81]  John A. Robinson,et al.  Structural Mimicry of Canonical Conformations in Antibody Hypervariable Loops Using Cyclic Peptides Containing a Heterochiral Diproline Template , 1999 .

[82]  Helen E Blackwell,et al.  Highly Efficient Synthesis of Covalently Cross-Linked Peptide Helices by Ring-Closing Metathesis. , 1998, Angewandte Chemie.

[83]  S. Kent,et al.  A novel method to synthesize cyclic peptides , 1998 .

[84]  Garland R. Marshall,et al.  Conformational Analysis of Reverse-Turn Constraints by N-Methylation and N-Hydroxylation of Amide Bonds in Peptides and Non-Peptide Mimetics , 1998 .

[85]  H. Nöth,et al.  Facile Synthesis of Cyclic Tetrapeptides from Nonactivated Peptide Esters on Metal Centers. , 1998, Angewandte Chemie.

[86]  A. Chamberlin,et al.  Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides. , 1997, Chemical reviews.

[87]  J. Tam,et al.  Metal ion-assisted peptide cyclization , 1997 .

[88]  James P. Tam,et al.  Synthesis and Application of Unprotected Cyclic Peptides as Building Blocks for Peptide Dendrimers , 1997 .

[89]  D. Fairlie,et al.  Conformational Control by Thiazole and Oxazoline Rings in Cyclic Octapeptides of Marine Origin. Novel Macrocyclic Chair and Boat Conformations. , 1997 .

[90]  D. Ryan,et al.  PSEUDO-PROLINES AS A MOLECULAR HINGE : REVERSIBLE INDUCTION OF CIS AMIDE BONDS INTO PEPTIDE BACKBONES , 1997 .

[91]  Michael Bienert,et al.  Cyclization of all-L-Pentapeptides by Means of 1-Hydroxy-7-azabenzotriazole-Derived Uronium and Phosphonium Reagents. , 1996, The Journal of organic chemistry.

[92]  D. Fairlie,et al.  Conformational control by thiazole and oxazoline rings in cyclic octapeptides of marine origin. Novel macrocyclic chair and boat conformations , 1996 .

[93]  J. Tam,et al.  Cyclic Peptides from Linear Unprotected Peptide Precursors through Thiazolidine Formation , 1996 .

[94]  Scott J. Miller,et al.  Application of Ring-Closing Metathesis to the Synthesis of Rigidified Amino Acids and Peptides , 1996 .

[95]  M. Mutter,et al.  Pseudo-Prolines as a Solubilizing, Structure-Disrupting Protection Technique in Peptide Synthesis , 1996 .

[96]  Horst Kessler,et al.  Cyclic RGD Peptides Containing β-Turn Mimetics , 1996 .

[97]  S. Akabori,et al.  Biomimetic Synthesis of Gramicidin S. Direct Formation of the Antibiotic from Pentapeptide Active Esters Having No Protecting Group on the Side Chain of the Orn Residue. , 1994 .

[98]  D. Hudson,et al.  A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides , 1993 .

[99]  D. Siri,et al.  Prediction of the best linear precursor in the synthesis of cyclotetrapeptides by molecular mechanic calculations , 1992 .

[100]  R. W. Hoffmann,et al.  Flexible Molecules with Defined Shape—Conformational Design , 1992 .

[101]  D. Seebach,et al.  Solubilization of Peptides in Non‐polar Organic Solvents by the Addition of Inorganic Salts: Facts and Implications , 1989 .

[102]  C. Li,et al.  New segment-coupling method for peptide synthesis in aqueous solution: application to synthesis of human [Gly17]-beta-endorphin. , 1981, Proceedings of the National Academy of Sciences of the United States of America.

[103]  D. Veber,et al.  Practical synthesis of cyclic peptides, with an example of dependence of cyclization yield upon linear sequence , 1979 .

[104]  S. Hentges,et al.  A Vanadium Carbonyl Trihydride, H3V(CO)3diars , 1977 .

[105]  M. Rothe,et al.  Synthesis of Cyclotri‐L‐prolyl, a Cyclotripeptide Having a Nine‐Membered Ring , 1965 .

[106]  G. F. Gause,et al.  Gramicidin S and its use in the Treatment of Infected Wounds , 1944, Nature.

[107]  S. Ingemann,et al.  Improved Auxiliary for the Synthesis of Medium-Sized Bis(lactams) , 2008 .

[108]  Valentina Aureggi 1,3-Dipolar cycloadditions , 2007 .

[109]  P. Merino 1,3-Dipolar Cycloadditions , 2004 .

[110]  J. Pelletier,et al.  A new tri-orthogonal strategy for peptide cyclization. , 2002, Organic letters.

[111]  T. Muir,et al.  Chemoselective backbone cyclization of unprotected peptides , 1997 .

[112]  T. Muir,et al.  Synthesis of proteins by native chemical ligation. , 1994, Science.

[113]  T. Y. Tsang Mechanisms and Applications , 1989 .

[114]  J. Smith,et al.  Reverse turns in peptides and proteins. , 1980, CRC critical reviews in biochemistry.

[115]  K. Kopple,et al.  Reverse Turns in Peptides and Protein , 1980 .

[116]  S. Mazur,et al.  Chemistry of polymer-bound o-benzyne. Frequency of encounter between substituents on crosslinked polystyrenes , 1979 .

[117]  J. Rebek,et al.  Organic chemistry on the solid phase. Site-site interactions on functionalized polystyrene , 1977 .

[118]  K. Lübke,et al.  THE SYNTHESIS OF CYCLIC PEPTIDES , 1965 .

[119]  R. Sheppard,et al.  Peptides—XIII : Effects of configuration on dielectric increments and cyclization of some simple peptides , 1963 .