Shape-programmable macromolecules

Accounts of Chemical Research

Volumn 41, Issue 10, 2008, Pages 1387-1398

  Schafmeister, Christian E ^a   Brown, Zachary Z ^a   Gupta, Sharad ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MACROMOLECULE; SPECTROSCOPY; SYNTHESIS;

AMINO ACIDS; MACROMOLECULAR SUBSTANCES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; SPECTRUM ANALYSIS;

EID: 57349150481     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700283y     Document Type: Article

References (31)

1. Lokey, R. S.; Iverson, B. L. Synthetic molecules that fold into a pleated secondary structure in solution. Nature 1995, 375, 303-305.
2. Dado, G. P.; Gellman, S. H. Intramolecular hydrogen-bonding in derivatives of β- alanine and γ-amino butyric-acid: Model studies for the folding of unnatural polypeptide backbones. J. Am. Chem. Soc. 1994, 116, 1054-1062.
3. AppellaD. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X.; Barchi, J. J., Jr.; Gellman, S. H. Residue-based control of helix shape in beta-peptide oligomers. Nature 1997, 387, 381-384.
4. Seebach, D.; Matthews, J. L. β-Peptides: A surprise at every turn. Chem. Commun. 1997, 21, 2015-2022.
5. Seebach, D.; Abele, S.; Gademann, K.; Jaun, B. Pleated sheets and turns of β-peptides with proteinogenic side chains. Angew. Chem., Int. Ed. 1999, 38, 1595-1597.
6. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Solvophobically driven folding of nonbiological oligomers. Science 1997, 277, 1793-1796.
7. Gellman, S. H. Foldamers: A manifesto. Acc. Chem. Res. 1998, 31, 173-180.
8. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. A field guide to foldamers. Chem. Rev. 2001, 101, 3893-4011.
9. Stoddart, J. F. Molecular Lego. Chem. Br. 1988, 24, 1203-1208.
10. Ashton, P. R.; Brown, G. R.; Isaacs, N. S.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Slawin, A. M. Z.; Smith, D. R.; Stoddart, J. F.; Williams, D. J. Molecular LEGO. 1. substrate-directed synthesis via stereoregular Diels-Alder oligomerizations. J. Am. Chem. Soc. 1992, 114, 6330-6353.
11. Levins, C. G.; Schafmeister, C. E. The synthesis of functionalized nanoscale molecular rods of defined length. J. Am. Chem. Soc. 2003, 125, 4702-4703.
12. Baker, G. L.; Fritschel, S. J.; Stille, J. R.; Stille, J. K. Transition-metal-catalyzed asymmetric organic-synthesis via polymer-attached optically-active phosphine-ligands. 5. Preparation of amino acids in high optical yield via catalytic-hydrogenation. J. Org. Chem. 1981, 46, 2954-2960.
13. Carpino, L. A. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J. Am. Chem. Soc. 1993, 115, 4397-4398.
14. Levins, C. G.; Schafmeister, C. E. The synthesis of curved and linear structures from a minimal set of monomers. J. Org. Chem. 2005, 70, 9002-9008.
15. Gund, P.; Veber, D. F. On the ease of base-catalyzed epimerization of N-methylated peptides and diketopiperazines. J. Am. Chem. Soc. 1979, 101, 1885-1887.
16. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A second generation force-field for the simulation of proteins, nucleic acids, and organic molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
17. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed.; Kluwer Academic/Plenum Publishers: New York, 1999.
18. Pomsuwan, S.; Bird, G.; Schafmeister, C. E.; Saxena, S. Flexibility and lengths of bis-peptide nanostructures by electron spin resonance. J. Am. Chem. Soc. 2006, 128, 3876-3877.
19. Martin, R. E.; Pannier, M.; Diederich, F.; Gramlich, V.; Hubrich, M.; Spiess, H. W. Determination of end-to-end distances in a series of TEMPO diradicals of up to 2.8 nm length with a new four-pulse double electron electron resonance experiment. Angew. Chem., Int. Ed. 1998, 37, 2834-2837.
20. Pornsuwan, S.; Schafmeister, C. E.; Saxena, S. Analysis of the dynamical flexibility of bis-peptide nanostructures. J. Phys. Chem. C 2008, 112, 1377-1384.
21. Habay, S. A.; Schafmeister, C. E. Synthesis of a bis-amino acid that creates a sharp turn. Org. Lett. 2004, 6, 3369-3371.
22. Wipf, P.; Kim, Y. T. Studies on the synthesis of stemona alkaloids - stereoselective preparation of the hydroindole ring-system by oxidative cyclization of tyrosine. Tetrahedron Lett. 1992, 33, 5477-5480.
23. Wipf, P.; Methot, J. L. Total synthesis and stereochemical revision of (+)-aeruginosin 298-A. Org. Lett. 2000, 2, 4213-4216.
24. Dominguez, C.; Ezquerra, J.; Baker, S. R.; Borrelly, S.; Prieto, L.; Espada, M.; Pedregal, C. Enantiospecific synthesis of (1S,2S,5R,6S)-2- aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid by a modified Corey-Link reaction. Tetrahedron Lett. 1998, 39, 9305-9308.
25. Pedregal, C.; Prowse, W. Stereoselective synthesis of 2-amino-3-fluoro bicyclo[3.1.0]hexane-2,6-dicarboxylic acid. Bioorg. Med. Chem. 2002, 10, 433-436.
26. Corey, E. J.; Link, J. O. A general, catalytic, and enantioselective synthesis of α-aminoacids. J. Am. Chem. Soc. 1992, 114, 1906-1908.
27. Gupta, S.; Das, B. C.; Schafmeister, C. E. Synthesis of a pipecolic acid-based bis-amino acid and its assembly into a spiro ladder oligomer. Org. Lett. 2005, 7, 2861-2864.
28. Pellicciari, R.; Natalini, B.; Luneia, R.; Marinozzi, M.; Roberti, M.; Rosato, G. C.; Sadeghpour, B. M.; Snyder, J. P.; Monahan, J. B.; Moroni, F. Enantioselective synthesis of naturally occurring trans-4-hydroxy-S-pipecolic acid-4-sulfate, a new potent and selective NMDA receptor agonist. Med. Chem. Res. 1992, 2, 491-496.
29. Baldwin, J. Rules for ring closure. Chem. Commun. 1976, 734-736.
30. Gupta, S.; Macala, M.; Schafmeister, C. E. Synthesis of structurally diverse bis-peptide oligomers. J. Org. Chem. 2006, 71, 8691-8695.
31. Schafmeister, C. E.; Belasco, L. G.; Brown, P. H. Observation of contraction and expansion in a bis-peptide based mechanical molecular actuator Chem. - Eur. J. 2008, 14(21), 6406-6412.