Solid-phase synthesis of N-substituted glycine oligomers (α-peptoids) and derivatives

Molecules

Volumn 15, Issue 8, 2010, Pages 5282-5335

  Culf, Adrian S ^a,b   Ouellette, Rodney J ^a  

^a ATLANTIC CANCER RESEARCH INSTITUTE   (Canada)

^b MOUNT ALLISON UNIVERSITY   (Canada)

Author keywords

N substituted polyglycine oligomer; Peptoid; Solid phase synthesis; Synthetic methods

Indexed keywords

DRUG DERIVATIVE; GLYCINE DERIVATIVE; SOLVENT;

ACYLATION; AMINATION; ARTICLE; CHEMISTRY; PROTEIN QUATERNARY STRUCTURE; SYNTHESIS;

ACYLATION; AMINATION; N-SUBSTITUTED GLYCINES; PROTEIN STRUCTURE, QUATERNARY; SOLVENTS;

EID: 77956101032     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15085282     Document Type: Article

References (227)

1. Simon, R.J.; Kania, R.S.; Zuckermann, R.N.; Huebner, V.D.; Jewell, D.A.; Banville, S.; Ng, S.; Wang, L.; Rosenberg, S.; Marlowe, C.K. Peptoids: A modular approach to drug discovery. Proc. Nat. Acad. Sci. USA 1992, 89, 9367-9371.
2. Zuckermann, R.N.; Kerr, J.M.; Kent, S.B.H.; Moos, W.H. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis. J. Am. Chem. Soc. 1992, 114, 10646-10647.
3. Figliozzi, G.M.; Goldsmith, R.; Ng, S.C.; Banville, S.C.; Zuckermann, R.N. Synthesis of Nsubstituted glycine peptoid libraries. Methods Enzymol. 1996, 267, 437-447.
4. Patch, J.A.; Kirshenbaum, K.; Seurynck, S.L.; Zuckermann, R.N.; Barron, A.E. Versatile Oligo(N-Subsitituted) Glycines: The Many Roles of Peptoids in Drug Discovery. In Pseudopeptides in Drug Discovery; Nielsen, P.E., Ed.; Wiley-VCH Verlag, GmbH & Co. KgaA: Weinheim, Germany, 2004; pp. 1-31.
5. Richter, L.S.; Spellmeyer, D.C.; Martin, E.J.; Figliozzi, G.M.; Zuckermann, R.N. Automated Synthesis of Nonnatural Oligomer Libraries: The Peptoid Concept. In Combinatorial Peptide and Nonpeptide Libraries; Jung, G., Ed.; VCH: Weinheim, Germany, 1996; pp. 387-404.
6. Murphy, J.E.; Uno, T.; Hamer, J.D.; Cohen, F.E.; Dwarki, V.; Zuckermann, R.N. A combinatorial approach to the discovery of efficient cationic peptoid reagents for gene delivery. Proc. Nat. Acad. Sci. USA 1998, 95, 1517-1522.
7. Lee, B.-C.; Zuckermann, R.N.; Dill, K.A. Folding a Nonbiological Polymer into a Compact Multihelical Structure. J. Am.Chem. Soc. 2005, 127, 10999-11009.
8. Lee, B.-C.; Dill, K.A.; Zuckermann, R.N. Synthesis of long non-natural sequence-specific heteropolymers. Polym. Preprints (Am. Chem. Soc., Div. Polym. Chem.) 2005, 46, 174-175.
9. Yoo, B.; Kirshenbaum, K. Protease-Mediated Ligation of Abiotic Oligomers. J. Am. Chem. Soc. 2005, 127, 17132-17133.
10. Kodadek, T.; Bachhawat-Sikder, K. Optimized protocols for the isolation of specific proteinbinding peptides or peptoids from combinatorial libraries displayed on beads. Mol. Biosyst. 2006, 2, 25-35.
11. Zuckermann R.N.; Kodadek T. Peptoids as potential therapeutics. Curr. Opin. Mol. Therap. 2009, 11, 299-307.
12. Léo, S.A.; Blackwell, H.E. Structure-function relationships in peptoids: Recent advances toward deciphering the structural requirements for biological function. Org. Biomol. Chem. 2009, 7, 1508-1524.
13. Masip, I.; Pérez-Payá, E.; Messeguer, A. Peptoids as source of compounds eliciting antibacterialactivity. Comb. Chem. & H.T.S. 2005, 8, 235-239.
14. Hinshaw, J.C.; Prestwich, G.D. The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: Peptoid molecular transporters. Chemtracts 2001, 14, 391-394.
15. Brown, N.J.; Johansson, J.; Barron, A.E. Biomimicry of Surfactant Protein C. Account Chem. Res. 2008, 41, 1409-1417.
16. Czyzewski, A.M.; Barron, A.E. Protein and peptide biomimicry: Gold-mining inspiration from Nature's ingenuity. AIChE J. 2008, 54, 1-7.
17. Astle, J.M.; Simpson, L.S.; Huang, Y.; Reddy, M.M.; Wilson, R.; Connell, S.; Wilson, J.; Kodadek, T. Seamless bead to microarray screening: Rapid identification of the highest affinity protein ligands from large combinatorial libraries. Chem. Biol. 2010, 17, 38-45.
18. Kwon, Y.-U.; Kodadek, T. Quantitative evaluation of the relative cell permeability of peptoids and peptides. J. Am. Chem. Soc. 2007, 129, 1508-1509.
19. Miller, S.M.; Simon, R.J.; Ng, S.; Zuckermann, R.N.; Kerr, J.M.; Moos, W.H. Comparison of the proteolytic susceptibilities of homologous L-amino acid, D-amino acid, and N-substituted glycine peptide and peptoid oligomers. Drug Develop. Res. 1995, 35, 20-32.
20. Miller, S.M.; Simon, R.J.; Ng, S.; Zuckermann, R.N.; Kerr, J.M.; Moos, W.H. Proteolytic studies of homologous peptide and N-substituted glycine peptoid oligomers. Bioorg. Med. Chem. Lett. 1994, 4, 2657-2662.
21. Lim, H.-S.; Muralidhar Reddy, M.; Xiao, X.; Wilson, J.; Wilson, R.; Connell, S.; Kodadek, T. Rapid identification of improved protein ligands using peptoid microarrays. Bioorg. Med. Chem. Lett. 2009, 19, 3866-3869.
22. Statz, A.R.; Kuang, J.; Ren, C.; Barron, A.E.; Szleifer, I.; Messersmith, P.B. Experimental and theoretical investigation of chain length and surface coverage on fouling of surface grafted polypeptoids. Biointerphases 2009, 4, FA22-FA32.
23. Zarra, R.; Montesarchio, D.; Coppola, C.; Bifulco, G.; Di Micco, S.; Izzo, I.; De Riccardis, F. Design, Synthesis, and Hybridisation of Water-Soluble, Peptoid Nucleic Acid Oligomers Tagged with Thymine. Eur. J. Org. Chem. 2009, 35, 6113-6120.
24. Dohm, M.T.; Seurynck-Servoss, S.L.; Seo, J.; Zuckermann, R.N.; Barron, A.E. Close mimicry of lung surfactant protein B by "clicked" dimers of helical, cationic peptoids. Biopolymers 2009, 92, 538-553.
25. Butterfoss, G.L.; Renfrew, P.D.; Kuhlman, B.; Kirshenbaum, K.; Bonneau, R. A preliminary survey of the peptoid folding landscape. J. Am. Chem. Soc. 2009, 131, 16798-16807.
26. Gorske, B.C.; Stringer, J.R.; Bastian, B.L.; Fowler, S.A.; Blackwell, H.E. New strategies for the design of folded peptoids revealed by a survey of noncovalent interactions in model systems. J. Am. Chem. Soc. 2009, 131, 16555-16567.
27. Maayan, G.; Ward, M.D.; Kirshenbaum, K. Folded biomimetic oligomers for enantioselective catalysis. Proc. Nat. Acad. Sci. USA 2009, 106, 13679-13684.
28. Norgren, A.S.; Budke, C.; Majer, Z.; Heggemann, C.; Koop, T.; Sewald, N. On-resin clickglycoconjugation of peptoids. Synthesis 2009, 488-494.
29. De Cola, C.; Licen, S.; Comegna, D.; Cafaro, E.; Bifulco, G.; Izzo, I.; Tecilla, P.; De Riccardis, F. Size-dependent cation transport by cyclic α-peptoid ion carriers. Org. Biomol. Chem. 2009, 7, 2851-2854.
30. Fisher, A.E.O.; Naughton, D.P. Novel peptoids for the detection and suppression of reactive oxygen and nitrogen species. Biochem. Soc. Trans. 2003, 31, 1302-1304.
31. Barron, A.E.; Zuckermann, R.N. Bioinspired polymeric materials: In-between proteins and plastics. Curr. Opin. Chem. Biol. 1999, 3, 681-687.
32. De Cola, C.; Licen, S.; Comegna, D.; Cafaro, E.; Bifulco, G.; Izzo, I.; Tecilla, P.; De Riccardis, F. Size-dependent cation transport by cyclic α-peptoid ion carriers. Org. Biomol. Chem. 2009, 7, 2851-2854.
33. Maayan, G.; Ward, M.D.; Kirshenbaum, K. Metallopeptoids. Chem. Commun. 2009, 56-58.
34. Shah, N.H.; Kirshenbaum, K. Photoresponsive peptoid oligomers bearing azobenzene side chains. Org. Biomol. Chem. 2008, 6, 2516-2521.
35. Holub, J.M.; Garabedian, M.J.; Kirshenbaum, K. Peptoids on steroids: precise multivalent estradiol - peptidomimetic conjugates generated via azide - alkyne [3 + 2] cycloaddition reactions. QSAR Comb. Sci. 2007, 26, 1175-1180.
36. Maayan, G.; Yoo, B.; Kirshenbaum, K. Heterocyclic amines for the construction of peptoid oligomers bearing multi-dentate ligands. Tetrahedron Lett. 2008, 49, 335-338.
37. Holub, J.M.; Jang, H.; Kirshenbaum, K. Clickity-click: highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support. Org. Biomol. Chem. 2006, 4, 1497-1502.
38. Jang, H.; Fafarman, A.; Holub, J.M.; Kirshenbaum, K. Click to Fit: Versatile Polyvalent Display on a Peptidomimetic Scaffold. Org. Lett. 2005, 7, 1951-1954.
39. Lee, J.; Udugamasooriya, D.G.; Lim, H.-S.; Kodadek, T. Potent and selective photo-inactivation of proteins with peptoid-ruthenium conjugates. Nat. Chem. Biol. 2010, 6, 258-260.
40. Qi, X.; Astle, J.; Kodadek, T. Rapid identification of orexin receptor binding ligands using cellbased screening accelerated with magnetic beads. Mol. Biosyst. 2010, 6, 102-107.
41. Sanborn, T.J.; Wu, C.W.; Zuckermann, R.N.; Barron, A.E. Extreme stability of helices formed by water-soluble poly-N-substituted glycines (polypeptoids) with α-chiral side chains. Biopolymers 2002, 63, 12-20.
42. Simpson, L.S.; Burdine, L.; Dutta, A.K.; Feranchak, A.P.; Kodadek, T. Selective Toxin Sequestrants for the Treatment of Bacterial Infections. J. Am. Chem. Soc. 2009, 131, 5760-5762.
43. Udugamasooriya, D.G.; Dineen, S.P.; Brekken, R.A.; Kodadek, T. A Peptoid "Antibody Surrogate" That Antagonizes VEGF Receptor 2 Activity. J. Am. Chem. Soc. 2008, 130, 5744-5752.
44. Lim, H.-S.; Archer, C.T.; Kodadek, T. Identification of a Peptoid Inhibitor of the Proteasome 19S Regulatory Particle. J. Am. Chem. Soc. 2007, 129, 7750-7751.
45. Xiao, X.; Yu, P.; Lim, H.-S.; Sikder, D.; Kodadek, T. Design and synthesis of a cell-permeable synthetic transcription factor mimic. J. Comb. Chem. 2007, 9, 592-600.
46. Astle, J.M.; Udugamasooriya, D.G.; Smallshaw, J.E.; Kodadek, T. A VEGFR2 Antagonist and Other Peptoids Evade Immune Recognition. Int. J. Pept. Res. Therap. 2008, 14, 223-227.
47. Udugamasooriya, D.G.; Dunham, G.; Ritchie, C.; Brekken, R.A.; Kodadek, T. The pharmacophore of a peptoid VEGF receptor 2 antagonist includes both side chain and main chain residues. Bioorg. Med. Chem. Lett. 2008, 18, 5892-5894.
48. Tan, N.C.; Yu, P.; Kwon, Y.-U.; Kodadek, T. High-throughput evaluation of relative cell permeability between peptoids and peptides. Bioorg. Med. Chem. 2008, 16, 5853-5861.
49. Shores, K.S.; Udugamasooriya, D.G.; Kodadek, T.; Knapp, D.R. Use of Peptide Analogue Diversity Library Beads for Increased Depth of Proteomic Analysis: Application to Cerebrospinal Fluid. J. Proteome Res. 2008, 7, 1922-1931.
50. Alluri, P.; Liu, B.; Yu, P.; Xiao, X.; Kodadek, T. Isolation and characterization of coactivatorbinding peptoids from a combinatorial library. Mol. Biosyst. 2006, 2, 568-579.
51. Liu, B.; Alluri, P.G.; Yu, P.; Kodadek, T. A Potent Transactivation Domain Mimic with Activity in Living Cells. J. Am. Chem. Soc. 2005, 127, 8254-8255.
52. Alluri, P.G.; Reddy, M.M.; Bachhawat-Sikder, K.; Olivos, H.J.; Kodadek, T. Isolation of protein ligands from large peptoid libraries. J. Am. Chem. Soc. 2003, 125, 13995-14004.
53. Li, S.; Bowerman, D.; Marthandan, N.; Klyza, S.; Luebke, K.J.; Garner, H.R.; Kodadek, T. Photolithographic Synthesis of Peptoids. J. Am. Chem. Soc. 2004, 126, 4088-4089.
54. Marthandan, N.; Klyza, S.; Li, S; Kwon, Y.U.; Kodadek, T; Garner, H.R. Construction and evaluation of an automated light directed protein-detecting microarray synthesizer. IEEE Trans. Nanobiosci. 2008, 7, 20-27.
55. Olivos, H.J.; Alluri, P.G.; Reddy, M.M.; Salony, D.; Kodadek, T. Microwave-Assisted Solid-Phase Synthesis of Peptoids. Org. Lett. 2002, 4, 4057-4059.
56. Fafarman, A.T.; Borbat, P.P.; Freed, J.H.; Kirshenbaum, K. Characterizing the structure and dynamics of folded oligomers: Pulsed ESR studies of peptoid helices. Chem. Commun. 2007, 377-379.
57. Shah, N.H.; Butterfoss, G.L.; Nguyen, K.; Yoo, B.; Bonneau, R.; Rabenstein, D.L.; Kirshenbaum, K. Oligo(N-aryl glycines): A new twist on structured peptoids. J. Am. Chem. Soc. 2008, 130, 16622-16632.
58. Shin, S.B.Y.; Kirshenbaum, K. Conformational Rearrangements by Water-Soluble Peptoid Foldamers. Org. Lett. 2007, 9, 5003-5006.
59. Yoo, B.; Kirshenbaum, K. Protease-Mediated Ligation of Abiotic Oligomers. J. Am. Chem. Soc. 2005, 127, 17132-17133.
60. Seo, J.; Barron, A.E.; Zuckermann, R.N. Novel Peptoid Building Blocks: Synthesis of Functionalized Aromatic Helix-Inducing Submonomers. Org. Lett. 2010, 12, 492-495.
61. Lee, B.-C.; Chu, T.K.; Dill, K.A.; Zuckermann, R.N. Biomimetic Nanostructures: Creating a High-Affinity Zinc-Binding Site in a Folded Nonbiological Polymer. J. Am. Chem. Soc. 2008, 130, 8847-8855.
62. Paulick, M.G.; Hart, K.M.; Brinner, K.M.; Tjandra, M.; Charych, D.H.; Zuckermann, R.N. Cleavable Hydrophilic Linker for One-Bead-One-Compound Sequencing of Oligomer Libraries by Tandem Mass Spectrometry. J. Comb. Chem. 2006, 8, 417-426.
63. Horn, T.; Lee, B.-C.; Dill, K.A.; Zuckermann, R.N. Incorporation of Chemoselective Functionalities into Peptoids via Solid-Phase Submonomer Synthesis. Bioconjugate Chem. 2004, 15, 428-435.
64. Burkoth, T.S.; Fafarman, A.T.; Charych, D.H.; Connolly, M.D.; Zuckermann, R.N. Incorporation of Unprotected Heterocyclic Side Chains into Peptoid Oligomers via Solid-Phase Submonomer Synthesis. J. Am. Chem. Soc. 2003, 125, 8841-8845.
65. Burkoth, T.S.; Beausoleil, E.; Kaur, S.; Tang, D.; Cohen, F.E.; Zuckermann, R.N. Toward the Synthesis of Artificial Proteins. The Discovery of an Amphiphilic Helical Peptoid Assembly. Chem. Biol. 2002, 9, 647-654.
66. Huang, C.-Y.; Uno, T.; Murphy, J.E.; Lee, S.; Hamer, J.D.; Escobedo, J.A.; Cohen, F.E.; Radhakrishnan, R.; Dwarki, V.; Zuckermann, R.N. Lipitoids - novel cationic lipids for cellular delivery of plasmid DNA in vitro. Chem. Biol. 1998, 5, 345-354.
67. Kirshenbaum, K.; Barron, A.E.; Goldsmith, R.A.; Armand, P.; Bradley, E.K.; Truong, K.T.V.; Dill, K.A.; Cohen, F.E.; Zuckermann, R.N. Sequence-specific polypeptoids: a diverse family of heteropolymers with stable secondary structure. Proc. Nat. Acad. Sci. USA 1998, 95, 4303-4308.
68. Zuckermann, R.N.; Martin, E.J.; Spellmeyer, D.C.; Stauber, G.B.; Shoemaker, K.R.; Kerr, J.M.; Figliozzi, G.M.; Goff, D.A.; Siani, M.A.; Simon, R.J.; Banville, S.C.; Brown, E.G.; Wang, L.; Richter, L.S.; Moos, W.H. Discovery of Nanomolar Ligands for 7-Transmembrane G-Protein-Coupled Receptors from a Diverse N-(Substituted)glycine Peptoid Library. J. Med. Chem. 1994, 37, 2678-2685.
69. Goff, D.A.; Zuckermann, R.N. Solid-phase synthesis of defined 1,4-benzodiazepine-2,5-dione mixtures. J.Org. Chem. 1995, 60, 5744-5745.
70. Messeguer, J.; Cortes, N.; Garcia-Sanz, N.; Navarro-Vendrell, G.; Ferrer-Montiel, A.; Messeguer, A. Synthesis of a positional scanning library of pentamers of N-alkylglycines assisted by microwave activation and validation via the identification of trypsin inhibitors. J. Comb. Chem. 2008, 10, 974-980.
71. Quintanar-Audelo, M.; Fernandez-Carvajal, A.; Van Den Nest, W.; Carreno, C.; Ferrer-Montiel, A.; Albericio, F. Design and Synthesis of Indole-Based Peptoids as Potent Noncompetitive Antagonists of Transient Receptor Potential Vanilloid 1. J. Med. Chem. 2007, 50, 6133-6143.
72. Mas-Moruno, C.; Cruz, L.J.; Mora, P.; Francesch, A.; Messeguer, A.; Perez-Paya, E.; Albericio, F. Smallest peptoids with antiproliferative activity on human neoplastic cells. J. Med. Chem. 2007, 50, 2443-2449.
73. Masip, I.; Cortes, N.; Abad, M.-J.; Guardiola, M.; Perez-Paya, E.; Ferragut, J.; Ferrer-Montiel, A.; Messeguer, A. Design and synthesis of an optimized positional scanning library of peptoids: identification of novel multidrug resistance reversal agents. Bioorg. Med. Chem. 2005, 13, 1923-1929.
74. Mora, P.; Masip, I.; Cortes, N.; Marquina, R.; Merino, R.; Merino, J.; Carbonell, T.; Mingarro, I.; Messeguer, A.; Perez-Paya, E. Identification from a Positional Scanning Peptoid Library of in vivo Active Compounds That Neutralize Bacterial Endotoxins. J. Med. Chem. 2005, 48, 1265-1268.
75. Humet, M.; Carbonell, T.; Masip, I.; Sanchez-Baeza, F.; Mora, P.; Canton, E.; Gobernado, M.; Abad, C.; Perez-Paya, E.; Messeguer, A. A positional scanning combinatorial library of peptoids as a source of biological active molecules: identification of antimicrobials. J. Comb. Chem. 2003, 5, 597-605.
76. Garcia-Martinez, C.; Humet, M.; Planells-Cases, R.; Gomis, A.; Caprini, M.; Viana, F.; De la Pena, E.; Sanchez-Baeza, F.; Carbonell, T.; De Felipe, C. Attenuation of thermal nociception and hyperalgesia by VR1 blockers. Proc. Nat. Acad. Sci. USA 2002, 99, 2374-2379.
77. Chongsiriwatana, N.P.; Patch, J.A.; Czyzewski, A.M.; Dohm, M.T.; Ivankin, A.; Gidalevitz, D.; Zuckermann, R.N.; Barron, A.E. Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides. Proc. Nat. Acad. Sci. USA 2008, 105, 2794-2799.
78. Statz, A.R.; Park, J.P.; Chongsiriwatana, N.P.; Barron, A.E.; Messersmith, P.B. Surfaceimmobilised antimicrobial peptoids. Biofouling 2008, 24, 439-448.
79. Brown, N.J.; Wu, C.W.; Seurynck-Servoss, S.L.; Barron, A.E. Effects of Hydrophobic Helix Length and Side Chain Chemistry on Biomimicry in Peptoid Analogues of SP-C. Biochemistry 2008, 47, 1808-1818.
80. Seurynck-Servoss, S.L.; Dohm, M.T.; Barron, A.E. Effects of Including an N-Terminal Insertion Region and Arginine-Mimetic Side Chains in Helical Peptoid Analogues of Lung Surfactant Protein B. Biochemistry 2006, 45, 11809-11818.
81. Seurynck, S.L.; Patch, J.A.; Barron, A.E. Simple, Helical Peptoid Analogs of Lung Surfactant Protein B. Chem. Biol. 2005, 12, 77-88.
82. Huang, K.; Wu, C.W.; Sanborn, T.J.; Patch, J.A.; Kirshenbaum, K.; Zuckermann, R.N.; Barron, A.E.; Radhakrishnan, I. A threaded loop conformation adopted by a family of peptoid nonamers. J. Am. Chem. Soc. 2006, 128, 1733-1738.
83. Patch, J.A.; Barron, A.E. Helical Peptoid Mimics of Magainin-2 Amide. J. Am. Chem. Soc. 2003, 125, 12092-12093.
84. Wu, C.W.; Sanborn, T.J.; Huang, K.; Zuckermann, R.N.; Barron, A.E. Peptoid oligomers with α-chiral, aromatic side chains: sequence requirements for the formation of stable peptoid helices. J. Am. Chem. Soc. 2001, 123, 6778-6784.
85. Fowler, S.A.; Luechapanichkul, R.; Blackwell, H.E. Synthesis and characterization of nitroaromatic peptoids: fine tuning peptoid secondary structure through monomer position and functionality. J. Org. Chem. 2009, 74, 1440-1449.
86. Gorske, B.C.; Jewell, S.A.; Guerard, E.J.; Blackwell, H.E. Expedient Synthesis and Design Strategies for New Peptoid Construction. Org. Lett. 2005, 7, 1521-1524.
87. Pokorski, J.K.; Miller Jenkins, L.M.; Feng, H.; Durell, S.R.; Bai, Y.; Appella, D.H. Introduction of a Triazole Amino Acid into a Peptoid Oligomer Induces Turn Formation in Aqueous Solution. Org. Lett. 2007, 9, 2381-2383.
88. Hara, T.; Durell, S.R.; Myers, M.C.; Appella, D.H. Probing the Structural Requirements of Peptoids That Inhibit HDM2-p53 Interactions. J. Am. Chem. Soc. 2006, 128, 1995-2004.
89. Unciti-Broceta, A.; Diezmann, F.; Ou-Yang, C.Y.; Fara, M.A.; Bradley, M. Synthesis, penetrability and intracellular targeting of fluorescein-tagged peptoids and peptide-peptoid hybrids. Bioorg. Med. Chem. 2009, 17, 959-966.
90. Diaz-Mochon, J.J.; Fara, M.A.; Sanchez-Martin, R.M.; Bradley, M. Peptoid dendrimersmicrowave-assisted solid-phase synthesis and transfection agent evaluation. Tetrahedron Lett. 2008, 49, 923-926.
91. Fara, M.A.; Diaz-Mochon, J.J.; Bradley, M. Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labeled peptides-a gentle heat goes a long way. Tetrahedron Lett. 2006, 47, 1011-1014.
92. Peretto, I.; Sanchez-Martin, R.M.; Wang, X.-H.; Ellard, J.; Mittoo, S.; Bradley, M. Cell penetrable peptoid carrier vehicles: synthesis and evaluation. Chem. Commun. 2003, 2312-2313.
93. Labuda, L.P.; Pushechnikov, A.; Disney, M.D. Small Molecule Microarrays of RNA-Focused Peptoids Help Identify Inhibitors of a Pathogenic Group I Intron. ACS Chem. Biol. 2009, 4, 299-307.
94. Disney, M.D.; Lee, M.M.; Pushechnikov, A.; Childs-Disney, J.L. The Role of Flexibility in the Rational Design of Modularly Assembled Ligands Targeting the RNAs that Cause the Myotonic Dystrophies. ChemBioChem 2010, 11, 375-382.
95. Comegna, D.; De Riccardis, F. An Efficient Modular Approach for the Assembly of S-Linked Glycopeptoids. Org. Lett. 2009, 11, 3898-3901.
96. De Cola, C.; Licen, S.; Comegna, D.; Cafaro, E.; Bifulco, G.; Izzo, I.; Tecilla, P.; De Riccardis, F. Size-dependent cation transport by cyclic α-peptoid ion carriers. Org. Biomol. Chem. 2009, 7, 2851-2854.
97. Elgersma, R.C.; Mulder, G.E.; Kruijtzer, J.A.W.; Posthuma, G.; Rijkers, D.T.S.; Liskamp, R.M.J. Transformation of the amyloidogenic peptide amylin(20-29) into its corresponding peptoid and retropeptoid: Access to both an amyloid inhibitor and template for self-assembled supramolecular tapes. Bioorg.Med. Chem. Lett. 2007, 17, 1837-1842.
98. Kruijtzer, J.A.W.; Hofmeyer, L.J.F.; Heerma, W.; Versluis, C.; Liskamp, R.M.J. Solid-phase syntheses of peptoids using Fmoc-protected N-substituted glycines: the synthesis of (retro)peptoids of leu-enkephalin and substance P. Chem.-Eur. J. 1998, 4, 1570-1580.
99. Hoffmann, B.; Ast, T.; Polakowski, T.; Reineke, U.; Volkmer, R. Transformation of a biologically active peptide into peptoid analogs while retaining biological activity. Prot. Pept. Lett. 2006, 13, 829-833.
100. Kesavan, V.; Tamilarasu, N.; Cao, H.; Rana, T.M. A new class of RNA-binding oligomers: Peptoid amide and ester analogues. Bioconjugate Chem. 2002, 13, 1171-1175.
101. Biondi, L.; Giannini, E.; Filira, F.; Gobbo, M.; Negri, L.; Rocchi, R. [D-Ala2]-deltorphin I peptoid and retropeptoid analogs: Synthesis, biological activity and conformational investigations. J. Pept. Sci. 2004, 10, 578-587.
102. Heine, N.; Ast, T.; Schneider-Mergener, J.; Reineke, U.; Germeroth, L.; Wenschuh, H. Synthesis and screening of peptoid arrays on cellulose membranes. Tetrahedron 2003, 59, 9919-9930.
103. Heine, N.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H.A modular approach to the SPOT synthesis of 1,3,5-trisubstituted hydantoins on cellulose membranes. Tetrahedron Lett. 2001, 42, 227-230.
104. Akamatsu, H.; Fukase, K.; Kusumoto, S. New Efficient Route for Solid-Phase Synthesis of Benzimidazole Derivatives. J. Comb. Chem. 2002, 4, 475-483.
105. Pirrung, M.C.; Park, K.; Tumey, L.N. 19F-Encoded Combinatorial Libraries: Discovery of Selective Metal Binding and Catalytic Peptoids. J. Comb. Chem. 2002, 4, 329-344.
106. Pirrung, M.C.; Park, K. Discovery of selective metal-binding peptoids using 19F encoded combinatorial libraries. Bioorg. Med. Chem. Lett. 2000, 10, 2115-2118.
107. Brown, D.S.; Revill, J.M.; Shute, R.E. Merrifield, alpha-methoxyphenyl (MAMP) resin; a new versatile solid support for the synthesis of secondary amides. Tetrahedron Lett. 1998, 39, 8533-8536.
108. Nnanabu, E.; Burgess, K. Cyclic semipeptoids: Peptoid-organic hybrid macrocycles. Org. Lett. 2006, 8, 1259-1262.
109. Ast, T.; Heine, N.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. Efficient assembly of peptomers on continuous surfaces. Tetrahedron Lett. 1999, 40, 4317-4318.
110. Anne, C.; Fournie-Zaluski, M.-C.; Roques, B.P.; Cornille, F. Solid phase synthesis of peptoid derivatives containing a free C-terminal carboxylate. Tetrahedron Lett. 1998, 39, 8973-8974.
111. Lee, M.M.; Pushechnikov, A.; Disney, M.D. Rational and modular design of potent ligands targeting the RNA that causes myotonic dystrophy 2. ACS Chem. Biol. 2009, 4, 345-355.
112. Chirayil, S.; Chirayil, R.; Luebke, K.J. Discovering ligands for a microRNA precursor with peptoid microarrays. Nucl. Acids Res. 2009, 37, 5486-5497.
113. Kwon, Y.-U.; Kodadek, T. Encoded combinatorial libraries for the construction of cyclic peptoid microarrays. Chem. Commun. 2008, 5704-5706.
114. Reddy, M.M.; Kodadek, T. Protein "fingerprinting" in complex mixtures with peptoid microarrays. Proc. Nat. Acad. Sci. USA 2005, 102, 12672-12677.
115. Svensson, A.; Bergquist, K.-E.; Fex, T.; Kihlberg, J. Fluorinated linkers for monitoring solidphase synthesis using gel-phase 19F NMR spectroscopy. Tetrahedron Lett. 1998, 39, 7193-7196.
116. Blommaert, A.G.S.; Weng, J.H.; Dorville, A.; McCort, I.; Ducos, B.; Durieux, C.; Roques, B.P. Cholecystokinin peptidomimetics as selective CCK-B antagonists: Design, synthesis, and in vitro and in vivo biochemical properties. J. Med. Chem. 1993, 36, 2868-2877.
117. Thompson, D.A.; Chai, B.-X.; Rood, H.L.E.; Siani, M.A.; Douglas, N.R.; Gantz, I.; Millhauser, G.L. Peptoid mimics of agouti related protein. Bioorg. Med. Chem. Lett. 2003, 13, 1409-1413.
118. Wagner, D.S.; Markworth, C.J.; Wagner, C.D.; Schoenen, F.J.; Rewerts, C.E.; Kay, B.K.; Geysen, H.M. Ratio encoding combinatorial libraries with stable isotopes and their utility in pharmaceutical research. Comb. Chem. HTS 1998, 1, 143-153.
119. Ng, S.; Goodson, B.; Ehrhardt, A.; Moos, W.H.; Siani, M.; Winter, J. Combinatorial discovery process yields antimicrobial peptoids. Bioorg. Med. Chem. 1999, 7, 1781-1785.
120. Taylor, E.W.; Gibbons, J.A.; Braeckman, R.A. Intestinal absorption screening of mixtures from combinatorial libraries in the Caco-2 model. Pharm. Res. 1997, 14, 572-577.
121. Nguyen, J.T.; Porter, M.; Amoui, M.; Miller, W.T.; Zuckermann, R.N.; Lim, W.A. Improving SH3 domain ligand selectivity using a non-natural scaffold. Chem. Biol. 2000, 7, 463-473.
122. Jacquot, Y.; Broutin, I.; Miclet, E.; Nicaise, M.; Lequin, O.; Goasdoue, N.; Joss, C.; Karoyan, P.; Desmadril, M.; Ducruix, A. High affinity Grb2-SH3 domain ligand incorporating Cβ-substituted prolines in a Sos-derived decapeptide. Bioorg. Med. Chem. 2007, 15, 1439-1447.
123. Goodson, B.; Ehrhardt, A.; Ng, S.; Nuss, J.; Johnson, K.; Giedlin, M.; Yamamoto, R.; Moos, W.H.; Krebber, A.; Ladner, M.; Giacona, M.B.; Vitt, C.; Winter, J. Characterization of novel antimicrobial peptoids. Antimicrob. Agents Chemother. 1999, 43, 1429-1434.
124. Holder, J.R.; Bauzo, R.M.; Xiang, Z.; Scott, J.; Haskell-Luevano, C. Design and pharmacology of peptoids and peptide-peptoid hybrids based on the melanocortin agonists core tetrapeptide sequence. Bioorg. Med. Chem. Lett. 2003, 13, 4505-4509.
125. Wu, C.W.; Sanborn, T.J.; Zuckermann, R.N.; Barron, A.E. Peptoid oligomers with α-chiral, aromatic side chains: effects of chain length on secondary structure. J. Am. Chem. Soc. 2001, 123, 2958-2963.
126. Wu, C.W.; Seurynck, S.L.; Lee, K.Y.C.; Barron, A.E. Helical Peptoid Mimics of Lung Surfactant Protein C. Chem. Biol. 2003, 10, 1057-1063.
127. Gorske, B.C.; Bastian, B.L.; Geske, G.D.; Blackwell, H.E. Local and tunable n→π interactions regulate amide isomerism in the peptoid backbone. J. Am. Chem. Soc. 2007, 129, 8928-8929.
128. Armand, P.; Kirshenbaum, K.; Goldsmith, R.A.; Farr-Jones, S.; Barron, A.E.; Truong, K.T.V.; Dill, K.A.; Mierke, D.F.; Cohen, F.E.; Zuckermann, R.N.; Bradley, E.K. NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains. Proc. Nat. Acad. Sci. USA 1998, 95, 4309-4314.
129. Lobo, B.A.; Vetro, J.A.; Suich, D.M.; Zuckermann, R.N.; Middaugh, C.R. Structure/function analysis of peptoid/lipitoid: DNA complexes. J. Pharma. Sci. 2003, 92, 1905-1918.
130. Uno, T.; Beausoleil, E.; Goldsmith, R.A.; Levine, B.H.; Zuckermann, R.N. New submonomers for poly N-substituted glycines (peptoids). Tetrahedron Lett. 1999, 40, 1475-1478.
131. Vicent, M.J.; Perez-Paya, E. Poly-L-glutamic acid (PGA) Aided Inhibitors of Apoptotic Protease Activating Factor 1 (Apaf-1): An Antiapoptotic Polymeric Nanomedicine. J. Med. Chem. 2006, 49, 3763-3765.
132. Pei, Y.; Moos, W.H. Post-modifications of peptoid side chains [3+2] cycloaddition of nitrile oxides with alkenes and alkynes on the solid-phase. Tetrahedron Lett. 1994, 35, 5825-5828.
133. Tang, Y.-C.; Deber, C.M. Aqueous solubility and membrane interactions of hydrophobic peptides with peptoid tags. Biopolymers 2004, 76, 110-118.
134. Garas, A.; Bremner, J.B.; Coates, J.; Deadman, J.; Keller, P.A.; Pyne, S.G.; Rhodes, D.I. Binaphthyl scaffolded peptoids via ring-closing metathesis reactions and their anti-bacterial activities. Bioorg. Med. Chem. Lett. 2009, 19, 3010-3013.
135. Nandel, F.S.; Saini, A. Conformational study of short peptoid models for future applications as potent antimicrobial compounds. Macromol. Theory Simul. 2007, 16, 295-303.
136. Wu, C.W.; Kirshenbaum, K.; Sanborn, T.J.; Patch, J.A.; Huang, K.; Dill, K.A.; Zuckermann, R.N.; Barron, A.E. Structural and Spectroscopic Studies of Peptoid Oligomers with α-Chiral Aliphatic Side Chains. J. Am. Chem. Soc. 2003, 125, 13525-13530.
137. Moe, G.R.; Granoff, D.M. Molecular mimetics of Neisseria meningitidis serogroup B polysaccharide. Int. Rev. Immun. 2001, 20, 201-220.
138. Wender, P.A.; Mitchell, D.J.; Pattabiraman, K.; Pelkey, E.T.; Steinman, L.; Rothbard, J.B. The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters. Proc. Nat. Acad. Sci. USA 2000, 97, 13003-13008.
139. Wu, C.W.; Seurynck, S.L.; Lee, K.Y.C.; Barron, A.E. Helical Peptoid Mimics of Lung Surfactant Protein C. Chem. Biol. 2003,10, 1057-1063.
140. Heizmann, G.; Felder, E.R. Synthesis of an N-3-guanidinopropylglycine (Narg) derivative as a versatile building block for solid-phase peptide and peptoid synthesis. Pept. Res. 1994, 7, 328-332.
141. Statz, A.R.; Meagher, R.J.; Barron, A.E.; Messersmith, P.B. New peptidomimetic polymers for antifouling surfaces. J. Am. Chem. Soc. 2005, 127, 7972-7973.
142. Seo, J.; Michaelian, N.; Owens, S.C.; Dashner, S.T.; Wong, A.J.; Barron, A.E.; Carrasco, M.R. Chemoselective and microwave-assisted synthesis of glycopeptoids. Org. Lett. 2009, 11, 5210-5213.
143. Robinson, G.M.; Taylor, E.W.; Smyth, M.R.; Lunte, C.E. Application of capillary electrophoresis to the separation of structurally diverse N-(substituted)-glycine-peptoid combinatorial mixtures. J. Chromatogr. B 1998, 705, 341-350.
144. Yuasa, H.; Honma, H.; Hashimoto, H.; Tsunooka, M.; Kojima-Aikawa, K. Pentamer is the minimum structure for oligomannosylpeptoids to bind to concanavalin A. Bioorg. Med. Chem. Lett. 2007, 17, 5274-5278.
145. Saha, U.K.; Roy, R. Glycosylated peptoids as prototypical HIV-1 protease inhibitors. Tetrahedron Lett. 1997, 38, 7697-7700.
146. Saha, U.K.; Roy, R. First synthesis of N-linked-glycopeptoid as new glycopeptidomimetics. Tetrahedron Lett. 1995, 36, 3635-3638.
147. Kim, J.M.; Roy, R. Oligomeric glycopeptidomimetics bearing the cancer related TN-antigen. Tetrahedron Lett. 1997, 38, 3487-3490.
148. Kim, J.M.; Roy, R. New prototypical O-linked glycopeptido-mimetics corresponding to the linkage region of proteoglycans. Carbohyd. Res. 1997, 298, 173-179.
149. Kim, J.M.; Roy, R. First synthesis of O-linked xylopeptoid as new glycopeptidomimetic of the carbohydrate-protein linkage region of proteoglycans. Carbohyd. Lett. 1996, 1, 465-468.
150. Saha, U.K.; Roy, R. Synthesis of new glycopeptidomimetics based on N-substituted oligoglycine bearing an N-linked lactoside side-chain. Chem. Commun. 1995, 2571-2573.
151. Roy, R.; Saha, U.K. Rational design of multivalent glycoconjugate ligands. Synthesis of libraries of conformationally flexible rotamers of poly-N-linked lactosyl glycines. Chem. Commun. 1996, 201-202.
152. Hu, Y.-J.; Roy, R. Cross-metathesis of N-alkenyl peptoids with O-or C-allyl glycosides. Tetrahedron Lett. 1999, 40, 3305-3308.
153. Yuasa, H.; Kamata, Y.; Kurono, S.; Hashimoto, H. Solid phase synthesis of oligomannopeptoids that mimic the concanavalin A-binding trimannoside. Bioorg. Med. Chem. Lett. 1998, 8, 2139-2144.
154. Garcia-Echeverria, C.; Lewis, C.; Robinson, J. Fibrinogen-derived peptide compounds with antiangiogenic activity. PCT Int. Appl. 2003, Pub. No. WO/2003/070769.
155. Schroeder, T.; Niemeier, N.; Afonin, S.; Ulrich, A.S.; Krug, H.F.; Bräse, S. Peptoidic Aminoand Guanidinium-Carrier Systems: Targeted Drug Delivery into the Cell Cytosol or the Nucleus. J. Med. Chem. 2008, 51, 376-379.
156. Dechantsreiter, M.A.; Burkhart, F.; Kessler, H. A stereoselective synthesis of a C-glycosylated peptoid building block. Tetrahedron Lett. 1998, 39, 253-254.
157. Daelemans, D.; Schols, D.; Witvrouw, M.; Pannecouque, C.; Hatse, S.; Van Dooren, S.; Hamy, F.; Klimkait, T.; De Clercq, E.; Vandamme, A.-M. A second target for the peptoid tat/transactivation response element inhibitor CGP64222: inhibition of human immunodeficiency virus replication by blocking CXC-chemokine receptor 4-mediated virus entry. Mol. Pharmacol. 2000, 57, 116-124.
158. Vreeland, W.N.; Barron, A.E. Free-solution capillary electrophoresis of polypeptoidoligonucleotide conjugates. Polym. Preprints 2000, 41, 1018-1019.
159. Robinson, G.M.; Manica, D.P.; Taylor, E.W.; Smyth, M.R.; Lunte, C.E. Development of a capillary electrophoretic separation of an N-(substituted)- glycine-peptoid combinatorial mixture. J. Chromatogr. B 1998, 707, 247-255.
160. Maulucci, N.; Izzo, I.; Bifulco, G.; Aliberti, A.; De Cola, C.; Comegna, D.; Gaeta, C.; Napolitano, A.; Pizza, C.; Tedesco, C.; Flot, D.; DeRiccardis, F. Synthesis, structures, and properties of nine-, twelve-, and eighteen-membered N-benzyloxyethyl cyclic α-peptoids. Chem. Commun. 2008, 3927-3929.
161. Armand, P.; Kirshenbaum, K.; Falicov, A.; Dunbrack, R.L.; Dill, K.A.; Zuckermann, R.N.; Cohen, F.E. Chiral N-substituted glycines can form stable helical conformations. Fold. Des. 1997, 2, 369-375.
162. Fowler, S.A.; Stacy, D.M.; Blackwell, H.E. Design and synthesis of macrocyclic peptomers as mimics of a quorum sensing signal from Staphylococcus aureus. Org. Lett. 2008, 10, 2329-2332.
163. Holub, J.M.; Jang, H.; Kirshenbaum, K. Fit To Be Tied: Conformation-Directed Macrocyclization of Peptoid Foldamers. Org. Lett. 2007, 9, 3275-3278.
164. Shin, S.B.Y.; Yoo, B.; Todaro, L.J.; Kirshenbaum, K. Cyclic peptoids. J. Am. Chem. Soc. 2007, 129, 3218-3225.
165. Roy, O.; Faure, S.; Thery, V.; Didierjean, C.; Taillefumier, C. Cyclic β-Peptoids. Org. Lett. 2008, 10, 921-924.
166. Boeijen, A.; Liskamp, R.M.J. Sequencing of peptoid peptidomimetics by Edman degradation. Tetrahedron Lett. 1998, 39, 3589-3592.
167. Thakkar, A.; Cohen, A.S.; Connolly, M.D.; Zuckermann, R.N.; Pei, D. High-Throughput Sequencing of Peptoids and Peptide-Peptoid Hybrids by Partial Edman Degradation and Mass Spectrometry. J. Comb. Chem. 2009, 11, 294-302.
168. Heerma, W.; Versluis, C.; de Koster, C.G.; Kruijtzer, J.A.W.; Zigrovic, I.; Liskamp, R.M.J. Comparing mass spectrometric characteristics of peptides and peptoids. Rapid Commun. Mass Spectrom. 1996, 10, 459-464.
169. Heerma, W.; Boon, J.-P.; Versluis, K. High-energy CID tandem mass spectra of peptides and peptoids: similarities and differences. Adv. Mass Spect. 1998, 14, D045890:1-D045890:11.
170. Heerma, W.; Boon, J.-P.J.L.; Versluis, C.; Kruijtzer, J.A.W.; Hofmeyer, L.J.F.; Liskamp, R.M.J. Comparing mass spectrometric characteristics of peptides and peptoids. J. Mass Spectrom. 1997, 32, 697-704.
171. Zambias, R.A.; Boulton, D.A.; Griffin, P.R. Microchemical structure determination of a peptoid covalently bound to a polymeric bead by matrix-assisted laser desorption ionization time-offlight mass spectrometry. Tetrahedron Lett. 1994, 35, 4283-4286.
172. Ruijtenbeek, R.; Versluis, C.; Heck, A.J.R.; Redegeld, F.A.M.; Nijkamp, F.P.; Liskamp, R.M.J. Characterization of a phosphorylated peptide and peptoid and peptoid-peptide hybrids by mass spectrometry. J. Mass Spectrom. 2002, 37, 47-55.
173. 13C resonances of Nsubstituted glycine peptoids. J. Magn. Reson., Series B 1996, 110, 195-197.
174. Gorske, B.C.; Blackwell, H.E. Tuning peptoid secondary structure with pentafluoroaromatic functionality: a new design paradigm for the construction of discretely folded peptoid structures. J. Am. Chem. Soc. 2006, 128, 14378-14387.
175. Hjelmgaard, T.; Faure, S.; Caumes, C.; De Santis, E.; Edwards, A.A.; Taillefumier, C. Convenient Solution-Phase Synthesis and Conformational Studies of Novel Linear and Cyclic α,β-Alternating Peptoids. Org. Lett. 2009, 11, 4100-4103.
176. Doi, M.; Kinoshita, K.; Asano, A.; Yoneda, R.; Kurihara, T.; Ishida, T.N. Benzyl-N-(tertbutyloxycarbonyl) glycine, an N-substituted glycine (peptoid) monomer. Acta Crystal. C 1998, C54, 1164-1165.
177. Aubin, S.; Martin, B.; Delcros, J.-G.; Arlot-Bonnemains, Y.; Baudy-Floc'h, M. Retro Hydrazinoazapeptoids as Peptidomimetics of Proteasome Inhibitors. J. Med. Chem. 2005, 48, 330-334.
178. Hamper, B.C.; Kesselring, A.S.; Parker, M.H.; Turner, J.A. Solid-phase synthesis of Di-β-peptoids from acrylate resin: N-acetyl-N-benzyl-β- alaninyl-N-benzyl-β-alanine. Solid-Phase Org. Synth. 2001, 1, 55-72.
179. Reddy, M.M.; Bachhawat-Sikder, K.; Kodadek, T. Transformation of Low-Affinity Lead Compounds into High-Affinity Protein Capture Agents. Chem. Biol. 2004, 11, 1127-1137.
180. Lim, H.-S.; Cai, D.; Archer, C.T.; Kodadek, T. Periodate-triggered cross-linking reveals Sug2/Rpt4 as the molecular target of a peptoid inhibitor of the 19S proteasome Regulatory Particle. J. Am. Chem. Soc. 2007, 129, 12936-12937.
181. Schroeder, T.; Quintilla, A.; Setzler, J.; Birtalan, E.; Wenzel, W.; Bräse, S. Joint experimental and theoretical investigation of the propensity of peptoids as drug carriers. WSEAS Trans. Biol. Biomed. 2007, 4, 145-148.
182. Foged, C.; Franzyk, H.; Bahrami, S.; Frokjaer, S.; Jaroszewski, J.W.; Nielsen, H.M.; Olsen, C.A. Cellular uptake and membrane-destabilizing properties of α-peptide/β-peptoid chimeras: lessons for the design of new cell-penetrating peptides. BBA-Biomembranes 2008, 1778, 2487-2495.
183. Lee, M.M.; Childs-Disney, J.L.; Pushechnikov, A.; French, J.M.; Sobczak, K.; Thornton, C.A.; Disney, M.D. Controlling the specificity of modularly assembled small molecules for RNA via ligand module spacing: Targeting the RNAs that cause myotonic muscular dystrophy. J. Am. Chem. Soc. 2009, 131, 17464-17472.
184. Orzaez, M.; Mondragon, L.; Marzo, I.; Sanclimens, G.; Messeguer, A.; Perez-Paya, E.; Vicent, M. J. Conjugation of a novel Apaf-1 inhibitor to peptide-based cell-membrane transporters: Effective methods to improve inhibition of mitochondria-mediated apoptosis. Peptides 2007, 28, 958-968.
185. Guo, L; Zhang, D. Cyclic Poly(α-peptoid)s and Their Block Copolymers from N-Heterocyclic Carbene-Mediated Ring-Opening Polymerizations of N-Substituted N-Carboxylanhydrides. J. Am. Chem. Soc. 2009, 131, 18072-18074.
186. Vaz, B.; Brunsveld, L. Stable helical peptoids via covalent side chain to side chain cyclization. Org. Biomol. Chem. 2008, 6, 2988-2994.
187. Goff, D.A.; Zuckermann, R.N. The synthesis of 2-oxopiperazines by intramolecular Michael addition on solid support. Tetrahedron Lett. 1996, 37, 6247-6250.
188. Lim, H.-S.; Archer, C.T.; Kim, Y.-C.; Hutchens, T.; Kodadek, T. Rapid identification of the pharmacophore in a peptoid inhibitor of the proteasome regulatory particle. Chem. Commun. 2008, 1064-1066.
189. Uchida, M.; McDermott, G.; Wetzler, M.; Le Gros, M.A.; Myllys, M.; Knoechel, C.; Barron, A.E.; Larabella, C. A. Soft X-ray tomography of phenotypic switching and the cellular response to antifungal peptoids in Candida albicans. Proc. Nat. Acad. Sci. USA 2009, 106, 19375-19380.
190. Vedel, L.; Bonke, G.; Foged, C.; Ziegler, H.; Franzyk, H.; Jaroszewski, J.W.; Olsen, C.A. Antiplasmodial and prehemolytic activities of α-peptide-β-peptoid chimeras. ChemBioChem 2007, 8, 1781-1784.
191. Olsen, C.A.; Bonke, G.; Vedel, L.; Adsersen, A.; Witt, M.; Franzyk, H.; Jaroszewski, J.W. α-Peptide/β-peptoid chimeras. Org. Lett. 2007, 9, 1549-1552.
192. Shuey, S.W.; Delaney, W.J.; Shah, M.C.; Scialdone, M.A. Antimicrobial β-peptoids by a block synthesis approach. Bioorg. Med. Chem. Lett. 2006, 16, 1245-1248.
193. Masip, I.; Perez-Paya, E.; Messeguer, A. Peptoids as source of compounds eliciting antibacterial activity. Comb. Chem. HTS 2005, 8, 235-239.
194. Klimkait, T.; Felder, E.R.; Albrecht, G.; Hamy, F. Rational optimization of a HIV-1 Tat inhibitor: rapid progress on combinatorial lead structures. Biotechnol. Bioeng. 1999, 61, 155-168.
195. Zuckermann, R.N.; Chu, T.K.; Nam, K.T. Novel biomimetic peptoid polymers. PCT Int. Appl. 2010, Pub. No. WO/2010/017412.
196. Heizmann, G.; Hildebrand, P.; Tanner, H.; Ketterer, S.; Pansky, A.; Froidevaux, S.; Beglinger, C.; Eberle, A.N. A combinatorial peptoid library for the identification of novel MSH and GRP/bombesin receptor ligands. J. Recept. Signal Transduct. Res. 1999, 19, 449-466.
197. Bellier, B.; McCort-Tranchepain, I.; Ducos, B.; Danascimento, S.; Meudal, H.; Noble, F.; Garbay, C.; Roques, B.P. Synthesis and Biological Properties of New Constrained CCK-B Antagonists: Discrimination of Two Affinity States of the CCK-B Receptor on Transfected CHO Cells. J. Med. Chem. 1997, 40, 3947-3956.
198. Kordik, C.P.; Sanfilippo, P.J. Discovery of nanomolar ligands for 7-transmembrane G-proteincoupled receptors from a diverse N-(substituted)glycine peptoid library. Chemtracts: Org. Chem. 1995, 8, 36-40.
199. Mutulis, F.; Mutule, I.; Liepinsh, E.; Yahorau, A.; Lapinsh, M.; Kopantshuk, S.; Veiksina, S.; Rinken, A.; Wikberg, J.E.S. N-alkylated dipeptide amides and related structures as imitations of the melanocortins' active core. Peptides 2005, 26, 1997-2016.
200. Ryan, R.R.; Katsuno, T.; Mantey, S.A.; Pradhan, T.K.; Weber, H.C.; Coy, D.H.; Battey, J.F.; Jensen, R.T. Comparative pharmacology of the nonpeptide neuromedin B receptor antagonist PD 168368. J. Pharmacol. Exp. Therap. 1999, 290, 1202-1211.
201. Guerrini, R.; Calo, G.; Bigoni, R.; Rizzi, A.; Varani, K.; Toth, G.; Gessi, S.; Hashiba, E.; Hashimoto, Y.; Lambert, D.G.; Borea, P.A.; Tomatis, R.; Salvadori, S.; Regoli, D. Further Studies on Nociceptin-Related Peptides: Discovery of a New Chemical Template with Antagonist Activity on the Nociceptin Receptor. J. Med. Chem. 2000, 43, 2805-2813.
202. Messeguer, J.; Masip, I.; Montolio, M.; del Rio, J.A.; Soriano, E.; Messeguer, A. Peptoids bearing tertiary amino residues in the n-alkyl side chains: synthesis of a potent inhibitor of Semaphorin 3A. Tetrahedron 2010, 66, 2444-2454.
203. Xiao, X.; Yu, P.; Lim, H.-S.; Sikder, D.; Kodadek, T. A cell-permeable synthetic transcription factor mimics. Angew. Chem., Int. Ed. 2007, 46, 2865-2868.
204. Cardoso, A.L.; Lopes, S.M.M.; Beja, A.M.; Silva, M.R.; de los Santos, J.M.; Pinho e Melo, T.M.V.D.; Palacios, F. New chiral building blocks of β-peptoid analogs. Tetrahedron 2009, 65, 9116-9124.
205. Bonke, G.; Vedel, L.; Witt, M.; Jaroszewski, J.W.; Olsen, C.A.; Franzyk, H. Dimeric building blocks for solid-phase synthesis of α-peptide-β- peptoid chimeras. Synthesis 2008, 2381-2390.
206. Olsen, C.A.; Lambert, M.; Witt, M.; Franzyk, H.; Jaroszewski, J.W. Solid-phase peptide synthesis and circular dichroism study of chiral β-peptoid homooligomers. Amino Acids 2008, 34, 465-471.
207. Combs, D.J.; Lokey, R.S. Extended peptoids: a new class of oligomers based on aromatic building blocks. Tetrahedron Lett. 2007, 48, 2679-2682.
208. Mejias, X.; Feliu, L.; Planas, M.; Bardaji, E. Synthesis of nucleobase-functionalized β-peptoids and β-peptoid hybrids. Tetrahedron Lett. 2006, 47, 8069-8071.
209. Norgren, A.S.; Zhang, S.; Arvidsson, P.I. Synthesis and circular dichroism spectroscopic investigations of oligomeric β-peptoids with α-chiral side chains. Org. Lett. 2006, 8, 4533-4536.
210. Baldauf, C.; Guenther, R.; Hofmann, H.-J. Helices in peptoids of α-and β-peptides. Phys. Biol. 2006, 3, S1-S9.
211. Shin, I.; Park, K. Solution-Phase Synthesis of Aminooxy Peptoids in the C to N and N to C Directions. Organic Lett. 2002, 4, 869-872.
212. Hamper, B.C.; Kolodziej, S.A.; Scates, A.M.; Smith, R.G.; Cortez, E. Solid Phase Synthesis of β-Peptoids: N-Substituted β-Aminopropionic Acid Oligomers. J. Org. Chem. 1998, 63, 708-718.
213. Kruijtzer, J.A.W.; Lefeber, D.J.; Liskamp, R.M.J. Approaches to the synthesis of ureapeptoid peptidomimetics. Tetrahedron Lett. 1997, 38, 5335-5338.
214. Mouna, A.M.; Nguyen, C.; Rage, I.; Xie, J.; Nee, G.; Mazaleyrat, J.P.; Wakselman, M. Preparation of N-Boc-N-alkyl glycines for peptoid synthesis. Synth. Commun. 1994, 24, 2429-2435.
215. Tal-Gan, Y.; Freeman, N.S.; Klein, S.; Levitzki, A.; Gilon, C. Synthesis and structure-activity relationship studies of peptidomimetic PKB/Akt inhibitors: The significance of backbone interactions. Bioorg. Med. Chem. 2010, 18, 2976-2985.
216. Pei, D. On-Bead Library Screening Made Easier. Chem. Biol. 2010, 17, 3-4.
217. Swayze, E.E. Secondary amide-based linkers for solid phase organic synthesis. Tetrahdron Lett. 1997, 38, 8465-8468.
218. Yoo, B.; Kirshenbaum, K. Peptoid architectures: elaboration, actuation, and application. Curr. Opin. Chem. Biol. 2008, 12, 714-721.
219. Hamy, F.; Felder, E.R.; Heizmann, G.; Lazdins, J.; Aboul-ela, F.; Varani, G.; Karn, J.; Klimkait, T. An inhibitor of the Tat/TAR RNA interaction that effectively suppresses HIV-1 replication. Proc. Nat. Acad. Sci. USA 1997, 94, 3548-3553.
220. Goff, D.A. A peptoid based synthesis of di-and tri-substituted 2-oxopiperazines on solid support. Tetrahedron Lett. 1998, 39, 1473-1476.
221. Goff, D.A.; Zuckermann, R.N. Solid-Phase Synthesis of Highly Substituted Peptoid 1(2H)-Isoquinolinones. J. Org. Chem. 1995, 60, 5748-5749.
222. Chongsiriwatana, N.; Patch, J.A.; Zuckermann, R.N.; Marcano, Y.; Czyzewski, A.; Barron, A.E. Ampetoids: Non-natural, sequence-specific peptoid oligomers with a biomimetic mechanism of bacterial killing. Pept. Sci. 2006, 43, 220-221.
223. St. Hilaire, P.M.; Alves, L.C.; Herrera, F.; Renil, M.; Sanderson, S.J.; Mottram, J.C.; Coombs, G.H.; Juliano, M.A.; Juliano, L.; Arevalo, J.; Meldal, M. Solid-Phase Library Synthesis, Screening, and Selection of Tight-Binding Reduced Peptide Bond Inhibitors of a Recombinant Leishmania mexicana Cysteine Protease B. J. Med. Chem. 2002, 45, 1971-1982.
224. Meyer, J.-P.; Davis, P.; Lee, K.B.; Porreca, F.; Yamamura, H.I.; Hruby,V.J. Synthesis Using a Fmoc-Based Strategy and Biological Activities of Some Reduced Peptide Bond Pseudopeptide Analogues of Dynorphin Al. J. Med. Chem. 1995, 38, 3462-3468.
225. Wang, Y; Lin, H.; Tullman, R.; Jewell, C.F.; Weetall, M.L.; Tse, F.L.S. Absorption and disposition of a tripeptoid and a tetrapeptide in the rat. Biopharm. Drug Dispos. 1999, 20, 69-75.
226. Nam, K.T.; Shelby, S.A.; Choi, P.H.; Marciel, A.B.; Chen, R.; Tan, L.; Chu, T.K.; Mesch, R.A.; Lee, B.-C.; Connolly, M.D.; Kisielowski C.; Zuckermann, R.N. Free-floating ultrathin twodimensional crystals from sequence-specific peptoid polymers. Nat. Mater. 2010, 9, 454-460.
227. Utku, Y.; Rohatgi, A.; Yoo, B.; Kirshenbaum, K.; Zuckermann, R.N.; Pohl, N.L. Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory. J. Chem. Educ. 2010, 87, 637-639.