A New Class of Foldamers Based on cis-γ-Amino-L-proline(491 views) Farrera-Sinfreu J, Zaccaro L, Vidal D, Salvatella X, Giralt E, Pons M, Albericio F, Royo M
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2004 May 19; 126(19): 6048-6057.
Keywords: Conformations, Constraint Theory, Hydrogen Bonds, Nuclear Magnetic Resonance, Solutions, Solvents, Conformational Restrictions, Foldamers, Proline Rings, Secondary Structures, Proteins, C Peptide, Gamma Aminoproline, Unclassified Drug, Aqueous Solution, Article, Chemical Structure, Circular Dichroism, Molecular Interaction, Protein Conformation, Protein Secondary Structure, Aminobutyric Acids, Indicators And Reagents, Isomerism, Magnetic Resonance Spectroscopy, Models, Oligopeptides, Protein Folding, Erratum,
Affiliations: *** IBB - CNR ***
Barcelona Biomed. Research Institute, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain
Combinatorial Chemistry Unit, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain
Laboratory of Biomolecular NMR, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain
Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1, 08028-Barcelona, Spain
Ist. di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134, Naples, Italy
References: Giralt, E., Royo, M., Kogan, M., Crespo, L., Sanclimens, G., Farrera, J., Pons, M., Albericio, F., Proline: A key building block in "de novo" designed peptide molecules (2001) Peptides Proceedings of the 17th American Peptide Symposium, pp. 432-434. , Houghten, R., Lebl, M., Eds., American Peptide Society: San Diego, C
noteAppella, D.H., Christianson, L.A., Karle, I.L., Powell, D.R., Gellman, S.H., (1996) J. Am. Chem. Soc., 118, pp. 13071-13072
Hill, D.J., Mio, M.J., Prince, R.B., Hughes, T.S., Moore, J.S., (2001) Chem. Rev., 101, pp. 3893-4011
noteAppella, D. H., Christianson, L. A., Karle, I. L., Powell, D. R., Gellman, S. H., (1996) J. Am. Chem. Soc., 118, pp. 13071-13072
Hill, D. J., Mio, M. J., Prince, R. B., Hughes, T. S., Moore, J. S., (2001) Chem. Rev., 101, pp. 3893-4011
Simon, R. J., Kania, R. S., Zuckermann, R. N., Huebner, V. D., Jewell, D. A., Banville, S., Ng, S., Bartlett, P. A., (1992) Proc. Natl. Acad. Sci. U. S. A., 89, pp. 9367-9371
Nielsen, P. E., (1999) Acc. Chem. Res., 32, pp. 624-630
Smith, A. B., Favor, D. A., Sprengeler, P. A., Guzm n, M. C., Carroll, P. J., Furst, G. T., Hirschmann, R., (1999) Bioorg. Med. Chem., 7, pp. 9-22
Prince, R. B., Saven, J. G., Wolynes, P. G., Moore, J. S., (1999) J. Am. Chem. Soc., 121, pp. 3114-3121
Nguyen, J. Q., Iverson, B. L., (1999) J. Am. Chem. Soc., 121, pp. 2639-2640
Gung, B. M., Zou, D., Stalcup, A. M., Cottrell, C. E., (1999) J. Org. Chem., 64, pp. 2176-2177
Cheng, R. P., DeGrado, W. F., (2001) J. Am. Chem. Soc., 123, pp. 5162-5163
Arvidsson, P. I., Frackenpohl, J., Seebach, D., (2003) Helv. Chim. Acta, 86, pp. 1522-1553
Raguse, T. L., Lai, J. R., Gellman, S. H., (2003) J. Am. Chem. Soc., 125, pp. 5592-5593
Cheng, R. P., Gellman, S. H., DeGrado, W. F., (2001) Chem. Rev., 101, pp. 3219-3232
Gademann, K., H ne, A., Rueping, M., Jaun, B., Seebach, D., (2003) Angew. Chem., Int. Ed., 42, pp. 1534-1537
Apella, D. H., Christianson, L. A., Klein, D. H., Powell, D. R., Huang, X. L., Barchi, J. J., Gellman, S. H., (1997) Nature, 387, pp. 381-384
Chung, Y. J., Christianson, L. A., Stanger, H. E., Powell, D. R., Gellman, S. H., (1998) J. Am. Chem. Soc., 120, pp. 10555-10556
Appella, D. H., Barchi Jr., J. J., Durell, S. R., Gellman, S. H., (1999) J. Am. Chem. Soc., 121, pp. 2309-2310
Motorina, I. A., Huel, C., Quiniou, E., Mispelter, J., Adjadj, E., Grierson, D. S., (2001) J. Am. Chem. Soc., 123, pp. 8-17
Martinek, T. A., T th, G. H., Vass, E., Holl si, M., F l p, F., (2002) Angew. Chem., Int. Ed., 41, pp. 1718-1721
Hart, S. A., Bahadoor, A. B. F., Matthews, E. E., Qui, X. L., Schepartz, A., (2003) J. Am. Chem. Soc., 125, pp. 4022-4023
Porter, E. A., Wang, X., Lee, H. -S., Weisblum, B., Gellman, S. H., (2000) Nature, 404, pp. 565-565
Raguse, T. L., Porter, E. A., Weisblum, B., Gellman, S. H., (2002) J. Am Chem. Soc., 124, pp. 12774-12785
Epand, R. F., Umezawa, N., Porter, E. A., Gellman, S. H., Epand, R. M., (2003) Eur. J. Biochem., 270, pp. 1240-1248
Garc a-Echever a, C., Ruetz, S., (2003) Bioorg. Med. Chem. Lett., 13, pp. 247-251
Gelman, M. A., Richter, S., Cao, H., Umezawa, N., Gellman, S. H., Rana, T. M., (2003) Org. Lett., 5, pp. 3563-3565
Bruckner, A. M., Garcia, M., Marsh, A., Gellman, S. H., Diederichsen, U., (2003) Eur. J. Org. Chem., pp. 3555-3561
Woll, M. G., Lai, J. R., Guzei, I. A., Taylor, S. J. C., Smith, M. E. B., Gellman, S. H., (2001) J. Am Chem. Soc., 123, pp. 11077-11078
Krautha ser, S., Christianson, L. A., Powell, D. R., Gellman, S. H., (1997) J. Am. Chem. Soc., 119, pp. 11719-11720
Abele, S., V gtli, K., Seebach, D., (1999) Helv. Chim. Acta, 82, pp. 1539-1155
Schreiber, J. V., Seebach, D., (2000) Helv. Chim. Acta, 83, pp. 3139-3151
Gl ttli, A., Daura, X., Seebach, D., Van Gunsteren, W. F., (2002) J. Am. Chem. Soc., 124, pp. 12972-12978
Langenhan, J. M., Guzei, I. A., Gellman, S. H., (2003) Angew. Chem. Int. Ed., 42, pp. 2402-2405
Huck, B. R., Langenhan, J. M., Gellman, S. H., (1999) Org. Lett., 1, pp. 1717-1720
Barchi Jr., J. J., Huang, X., Appella, D. H., Christianson, L. A., Durell, S. R., Gellman, S. H., (2000) J. Am. Chem. Soc., 122, pp. 2711-2718
Huck, B. R., Fisk, J. D., Gellman, S. H., (2000) Org. Lett., 2, pp. 2607-2610
Chung, Y. J., Huck, B. R., Christianson, L. A., Stanger, H. E., Krauth user, S., Powell, D. R., Gellman, S. H., (2000) J. Am. Chem. Soc., 122, pp. 3995-4004
Le Plae, P. R., Fisk, J. D., Porter, E. A., Weisblum, B., Gellman, S. H., (2002) J. Am. Chem. Soc., 124, pp. 6820-6821
Park, J. -S., Lee, H. -S., Lai, J. R., Kim, B. M., Gellman, S. H., (2003) J. Am. Chem. Soc., 125, pp. 8539-8545
Woll, M. G., Fisk, J. D., Le Plae, P. R., Gellman, S. H., (2002) J. Am. Chem. Soc., 124, pp. 12447-12452
A New Class of Foldamers Based on cis-γ-Amino-L-proline
A synthetic method for the preparation of conformationally constrained γ-peptides derived from γ-amino-L-proline is described. The methodology allows the independent buildup of the peptide backbone and the introduction of sequential variations by reactions with the γ-amino group of γ-aminoproline. Both alkyl- and acyl-substituted γ-peptides have been prepared and studied by CD and NMR. Conformational restrictions due to the cyclic structure of the monomer give rise to long-range interactions that are indicative of secondary structures even in aqueous solution. Interresidue NOEs suggest a concatenation of turns that, in a permissive solvent, could give rise to an isolated hydrogen bond ribbon, flanked and protected by proline rings.
A New Class of Foldamers Based on cis-γ-Amino-L-proline
Antonini A, Vitale C, Barone P, Cilia R, Righini A, Bonuccelli U, Abbruzzese G, Ramat S, Petrone A, Quatrale R, Marconi R, Ceravolo R, Stefani A, Lopiano L, Zappia M, Capus L, Morgante L, Tamma F, Tinazzi M, Colosimo C, Guerra UP, Valzania F, Fagioli G, Distefano A, Bagnato A, Feggi L, Anna S, Maria Teresa Rosaria De Cr, Nobili F, Mazzuca N, Baldari S, Eleopra R, Bestetti A, Benti R, Varrone A, Volterrani D, Massa R, Stocchi F, Schillaci O, Dore F, Zibetti M, Castellano G, Battista SG, Giorgetti G * The relationship between cerebral vascular disease and parkinsonism: The VADO study(496 views) Parkinsonism Relat D (ISSN: 1353-8020, 1873-5126, 1873-5126electronic), 2012; 18(6): 775-780. Impact Factor:3.274 ViewExport to BibTeXExport to EndNote
Hesse B, Tagil K, Cuocolo A, Anagnostopoulos C, Bardies M, Bax J, Bengel F, Busemann Sokole E, Davies G, Dondi M, Edenbrandt L, Franken P, Kjaer A, Knuuti J, Lassmann M, Ljungberg M, Marcassa C, Marie PY, Mckiddie F, O'connor M, Prvuolovich E, Underwood R * 3. 0 T perfusion MR imaging(726 views) Rivista Di Neuroradiologia (ISSN: 1120-9976), 2004; 17(6): 807-812. Impact Factor:0.023 ViewExport to BibTeXExport to EndNote