Abstract
An X-ray diffraction analysis of the [Fmoc0,TOAC4,8, Leu-OMe11] analogue of thelipopeptaibol antibiotic trichogin A IV shows that the undecapeptide isfolded in a right-handed, mixed α/310-helix. The helicalmolecules are connected in a head-to-tail arrangement along the b-axisthrough C=O···H-N intermolecular H-bonding. Thispacking mode generates a hydrophobic cavity where the FmocNα-protecting groups are accommodated. The distances andangles between the nitroxide groups of the two TOAC residues, separated byone turn of the α-helix, have been determined.
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REFERENCES
Auvin-Guette, C., Rebuffat, S., Prigent, Y. and Bodo, B., J. Am. Chem. Soc., 114 (1992) 2170.
Benedetti, E., Bavoso, B., Di Blasio, B., Pavone, V., Pedone, C., Toniolo, C. and Bonora, G.M., Proc. Natl. Acad. Sci. USA, 79 (1982) 7951.
Toniolo, C., Crisma, M., Formaggio, F., Peggion, C., Monaco, V., Goulard, C., Rebuffat, S. and Bodo, B., J. Am. Chem. Soc., 118 (1996) 4952.
Toniolo, C., Peggion, C., Crisma, M., Formaggio, F., Shui, X. and Eggleston, D.S., Nat. Struct. Biol., 1 (1994) 908.
Toniolo, C. and Benedetti, E., Trends Biochem. Sci., 16 (1991) 350.
Hanson, P., Martinez, G., Millhauser, G., Formaggio, F., Crisma, M., Toniolo, C. and Vita, C., J. Am. Chem. Soc., 118 (1996) 271.
Hanson, P., Millhauser, G., Formaggio, F., Crisma, M. and Toniolo, C., J. Am. Chem. Soc., 118 (1996) 7618.
Karle, I.L. and Balaram, P., Biochemistry, 29 (1990) 6747.
Toniolo, C. and Benedetti, E., Macromolecules, 24 (1991) 2004.
Toniolo, C., Valente, E., Formaggio, F., Crisma, M., Pilloni, G., Corvaja, C., Toffoletti, A., Martinez, G.V., Hanson, M.P., Millhauser, G.L., George, C. and Flippen-Anderson, J.L., J. Pept. Sci., 1 (1995) 45.
Flippen-Anderson, J.L., George, C., Valle, G., Valente, E., Bianco, A., Formaggio, F., Crisma, M. and Toniolo, C., Int. J. Pept. Protein Res., 47 (1996) 231.
Monaco, V., Ph.D. Thesis, Department of Organic Chemistry, University of Padova, Italy, 1996.
Sheldrick, G.M., SHELXS 86, Program for the Solution of Crystal Structures, University of GÖttingen, GÖttingen, Germany, 1985.
Sheldrick, G.M., SHELXL v. 5.03, Siemens Analytical X-Ray Instruments Inc., Madison, WI, U.S.A., 1995.
IUPAC-IUB Commission on Biochemical Nomenclature, J. Mol. Biol., 52 (1970) 1.
Valle, G., Bonora, G.M. and Toniolo, C., Can. J. Chem., 62 (1984) 2661.
Benedetti, E., In Weinstein, B. (Ed.) Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, Vol. 6, Marcel Dekker, New York, NY, U.S.A., 1982, pp. 105–184.
Ashida, T., Tsunogae, Y., Tanaka, I. and Yamane, T., Acta Crystallogr., B43 (1987) 212.
Schweizer, W.B. and Dunitz, J.D., Helv. Chim. Acta, 65 (1982) 1547.
Paterson, Y., Rumsey, S.M., Benedetti, E., Némethy, G. and Scheraga, H.A., J. Am. Chem. Soc., 103 (1981) 2947.
Valle, G., Crisma, M., Formaggio, F., Toniolo, C. and Jung, G., Liebigs Ann. Chem., (1987) 1055.
Venkatachalam, C.M., Biopolymers, 6 (1968) 1425.
Toniolo, C., Crit. Rev. Biochem., 9 (1980) 1.
Rose, G.D., Gierasch, L.D. and Smith, J.A., Adv. Protein Chem., 37 (1985) 1.
Ramakrishnan, C. and Prasad, N., Int. J. Protein Res., 3 (1971) 209.
Taylor, R., Kennard, O. and Versichel, W., Acta Crystallogr., B40 (1984) 280.
Görbitz, C.M., Acta Crystallogr., B45 (1989) 390.
Pavone, V., Gaeta, G., Lombardi, A., Nastri, F., Maglio, O., Isernia, C. and Saviano, M., Biopolymers, 38 (1996) 705.
Toniolo, C., Bonora, G.M., Bavoso, A., Benedetti, E., Di Blasio, B., Pavone, V. and Pedone, C., Biopolymers, 22 (1983) 205.
Cremer, D. and Pople, J.A., J. Am. Chem. Soc., 97 (1975) 1354.
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Crisma, M., Monaco, V., Formaggio, F. et al. Crystallographic structure of a helical lipopeptaibol antibiotic analogue. Letters in Peptide Science 4, 213–218 (1997). https://doi.org/10.1023/A:1008874816982
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DOI: https://doi.org/10.1023/A:1008874816982