Department of Organic Chemistry, Institute of Biomolecular Chemistry, University of Padova, 35131 Padova, Italy
DSM Research, Life Sci., Adv. Synthesis/Catalysis, P.O. Box 18, 6160 MD Geleen, Netherlands
Laboratory of Crystallography, ESA 7036, Univ. Henry Poincaré-Nancy I, 54506 Vandoeuvre-lès-Nancy, France
Interuniv. Res. Ctr. Bioactive P., Inst. of Biostructure and Bioimaging, University of Naples Federico II, 80134 Naples, Italy
References: Polese, A., Mondini, S., Bianco, A., Toniolo, C., Scorrano, G., Guldi, G.M., Maggini, M., (1999) J. Am. Chem. Soc., 121, p. 344
Pispisa, B., Stella, L., Venanzi, M., Palleschi, A., Viappiani, C., Polese, A., Formaggio, F., Toniolo, C., (2000) Macromolecules, 33, p. 906
Antonello, S., Formaggio, F., Moretto, A., Toniolo, C., Maran, F., (2003) J. Am. Chem. Soc., 125, p. 2874
Karle, I.L., Balaram, P., (1990) Biochemistry, 29, p. 6747
Toniolo, C., Crisma, M., Formaggio, F., Valle, G., Cavicchioni, G., Précigoux, G., Aubry, A., Kamphuis, J., (1993) Biopolymers, 33, p. 1061
Venkatachalam, C.M., (1968) Biopolymers, 6, p. 1425
Toniolo, C., (1980) Crit. Rev. Biochem., 9, p. 1
Rose, G.D., Gierasch, L.M., Smith, J.P., (1985) Adv. Protein Chem., 37, p. 1
Formaggio, F., Crisma, M., Bonora, G.M., Pantano, M., Valle, G., Toniolo, C., Aubry, A., Kamphuis, J., (1995) J. Pept. Res., 8, p. 6
Jaun, B., Tanaka, M., Seiler, P., Kühnle, F.N.M., Braun, C., Seebach, D., (1997) Liebigs Ann., p. 1697
Yoder, G., Polese, A., Silva, R.A.G.D., Formaggio, F., Crisma, M., Broxterman, Q.B., Kamphuis, J., Keiderling, T.A., (1997) J. Am. Chem. Soc., 119, p. 10278
Mammi, S., Rainaldi, M., Bellanda, M., Schievano, E., Peggion, E., Broxterman, Q.B., Formaggio, F., Toniolo, C., (2000) J. Am. Chem. Soc., 122, p. 11735
Moretto, A., Peggion, C., Formaggio, F., Crisma, M., Toniolo, C., Piazza, C., Kaptein, B., Cativiela, C., (2000) J. Pept. Res., 56, p. 283
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Spagna, R., (1999) J. Appl. Crystallogr., 32, p. 115
Sheldrick, G.M., (1997) SHELXL 97: Program for Crystal Structure Refinement, , University of Göttingen: Göttingen, Germany
Cromer, D.T., Waber, J.T., (1974) International Tables for X-ray Crystallography, 2nd Ed., 4. , Kynoch Press: Birmingham, U.K., Table 2.2B (now distributed by D. Reidel Publ. Co., Dordrecht, The Netherlands)
Ramakrishnan, C., Prasad, N., (1971) Int. J. Protein Res., 3, p. 209
Taylor, R., Kennard, O., Versichel, W., (1984) Acta Crystallogr., Sect. B, 40, p. 280
Görbitz, C.H., (1989) Acta Crystallogr., Sect. B, 45, p. 390
Dunitz, J.D., Strickler, P., (1968) Structural Chemistry and Molecular Biology, pp. 595-602. , Rich, A., Davidson, N., Eds.
Freeman: San Francisco
Millhauser, G. L., (1995) Biochemistry, 34, p. 3873
Bolin, K. A., Millhauser, G. L., (1999) Acc. Chem. Res., 32, p. 1027
Karle, I. L., Balaram, P., (1990) Biochemistry, 29, p. 6747
Venkatachalam, C. M., (1968) Biopolymers, 6, p. 1425
Rose, G. D., Gierasch, L. M., Smith, J. P., (1985) Adv. Protein Chem., 37, p. 1
Sheldrick, G. M., (1997) SHELXL 97: Program for Crystal Structure Refinement, , University of G ttingen: G ttingen, Germany
Cromer, D. T., Waber, J. T., (1974) International Tables for X-ray Crystallography, 2nd Ed., 4. , Kynoch Press: Birmingham, U. K., Table 2. 2B (now distributed by D. Reidel Publ. Co., Dordrecht, The Netherlands)
Kruizinga, W. H., Bolster, J., Kellogg, R. M., Kamphuis, J., Boesten, W. H. J., Meijer, E. M., Schoemaker, H. E., (1988) J. Org. Chem., 53, p. 1826
Elferink, V. H. M., Breitgoff, D., Kloosterman, M., Kamphuis, J., Van den Tweel, W. J. J., Meijer, E. M., (1991) Reel. Tray. Chim. Pays-Bas, 110, p. 63
Schoemaker, H. E., Boesten, W. H. J., Kaptein, B., Hermes, H. F. M., Sonke, T., Broxterman, Q. B., Van den Tweel, W. J. J., Kamphuis, J., (1992) Pure Appl. Chem., 64, p. 1171
Chen, C. S., Fujimoto, Y., Girdaukas, G., Sih, C. J., (1982) J. Am. Chem. Soc., 104, p. 7294
Carpino, L. A., (1993) J. Am. Chem. Soc., 115, p. 4397
Carpino, L. A., Mansour, E. S. M. E., Sadat-Aalaee, D., (1991) J. Org. Chem., 56, p. 2611
Jones, D. S., Kenner, G. W., Preston, J., Sheppard, R. C., (1965) J. Chem. Soc., p. 6227
Br ckner, H., (1989) Chemistry of Peptides and Proteins, 4, pp. 79-86. , K nig, W. A., Voelter, W., Eds.
Attempto: T bingen, Germany
Cung, M. T., Marraud, M., N el, J., (1972) Ann. Chim. (Paris), p. 183
Bonora, G. M., Mapelli, C., Toniolo, C., Wilkening, R. R., Stevens, E. S., (1984) Int. J. Biol. Macromol., 6, p. 179
Kopple, K. D., Ohnishi, M., Go, A., (1969) Biochemistry, 8, p. 4087
Kopple, K. D., Schamper, T. J., (1972) J. Am. Chem. Soc., 94, p. 3644
(1970) J. Mol. Biol., 52, p. 1
Schweizer, W. B., Dunitz, J. D., (1982) Helv. Chim. Acta, 65, p. 1547
Zimmerman, S. S., Pottle, M. S., N methy, G., Scheraga, H. A., (1977) Macromolecules, 10, p. 1
G rbitz, C. H., (1989) Acta Crystallogr., Sect. B, 45, p. 390
Dunitz, J. D., Strickler, P., (1968) Structural Chemistry and Molecular Biology, pp. 595-602. , Rich, A., Davidson, N., Eds.
Cα-Methyl, Cα-n-Propylglycine Homo-oligomers
A series of Nα-protected, monodispersed homo-oligopeptide esters to the octamer level from L-Cα-methyl, C α-n-propylglycine [or Cα-methylnorvaline, (αMe)Nva] has been synthesized by solution methods and fully characterized. The preferred conformation of these homo-oligomers in solution has been assessed by FT-IR absorption and 1H NMR techniques. Moreover, the molecular structures of the homotrimer and homotetramer have been determined in the crystal state by X-ray diffraction. The obtained results strongly support the view that right-handed, single or multiple, and consecutive β bends are preferentially adopted by the conformationally restricted L-(αMe)Nva homo-oligomers. In particular, 310 helices are formed by the longest homo-oligomers. It is our contention that the [(αMe)Nva]n peptides represent the best available choice among Cα-trasubstituted α-amino acid-based homo-oligomers for the construction of relatively easy to make, rigid foldamers with a well-defined screw-sense bias.
Kállay C, Dávid A, Timári S, Nagy EM, Sanna D, Garribba E, Micera G, De Bona P, Pappalardo G, Rizzarelli E, Sóvágó I * Copper(II) complexes of rat amylin fragments(357 views) Dalton T (ISSN: 1477-9234, 1477-9226, 1477-9234electronic), 2011 Oct 14; 40(38): 9711-9721. Impact Factor:3.838 ViewExport to BibTeXExport to EndNote