Total synthesis and membrane modifying properties of the lipopeptaibol trikoningin KB II and its analogues with acyl chains of different length at the N- and C-termini

Journal of Peptide Science

Volumn 5, Issue 2, 1999, Pages 96-102

  Piazza, Claudia ^a   Formaggio, Fernando ^a   Crisma, Marco ^a   Toniolo, Claudio ^a   Kamphuis, Johan ^b   Kaptein, Bernard ^c   Broxterman, Quirinus B ^c  

^a UNIVERSITY OF PADOVA   (Italy)

^b DSM RESOLVE   (Netherlands)

^c DSM RESEARCH   (Netherlands)

Author keywords

Fatty acid; Lipopeptaibol; Membrane activity; Peptide synthesis

Indexed keywords

AMINO ACID; AMINOALCOHOL; LEUCINE; PEPTAIBOL; PEPTIDE;

ACYLATION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG STRUCTURE; MEMBRANE BIOLOGY; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; TRICHODERMA;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; CELL MEMBRANE PERMEABILITY; GLYCOPEPTIDES; LIPOSOMES; PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032951149     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199902)5:2<96::AID-PSC185>3.0.CO;2-G     Document Type: Article

References (30)

1. E. Benedetti, A. Bavoso, B. Di Blasio, V. Pavone, C. Pedone, C. Toniolo and G.M. Bonora (1982). Peptaibol antibiotics. A study on the helical structure of the 2-9 sequence of emerimicins III and IV. Proc. Natl. Acad. Sci. USA 79, 7951-7954.
2. R. Nagaraj and P. Balaram (1981). Alamethicin, a transmembrane channel. Acc. Chem. Res. 14, 356-362.
3. C. Auvin-Guette, S. Rebuffat, Y. Prigent and B. Bodo (1992). Trichogin A IV, an 11-residue lipopeptaibol from Trichoderma longibrachiatum. J. Am. Chem. Soc. 114, 2170-2174.
4. C. Toniolo, C. Peggion, M. Crisma, F. Formaggio, X. Shui and D.S. Eggleston (1994). Structure determination of racemic trichogin A IV using centrosymmetric crystals. Nature: Struct. Biol. 1, 908-914.
5. x-acyl chain length on the membrane-modifying properties of synthetic analogs of the lipopeptaibol trichogin GA IV. J. Am. Chem. Soc. 118, 4952-4958.
6. P. Scrimin, A. Veronese, P. Tecilla, U. Tonellato, V. Monaco, F. Formaggio, M. Crisma and C. Toniolo (1996). Metal ion modulation of membrane permeability induced by a polypeptide template. J. Am. Chem. Soc. 118, 2505-2506.
7. X. Shui, D.S. Eggleston, V. Monaco, F. Formaggio, M. Crisma and C. Toniolo. Amphipathic peptide helices. Structure of a trichogin A IV analog containing serine, Octanoyl-Aib-Ser-Leu-Aib-Ser-Ser-Leu-Aib-Ser-Ile-Leu-OMe, in: Peptides: Chemistry, Structure and Biology, P.T.P. Kaumaya and R.S. Hodges, Eds, p. 436-437, Mayflower Scientific, Kingswinford, UK, 1996.
8. M. Crisma, V. Monaco, F. Formaggio, C. Toniolo, C. George and J.L. Flippen-Anderson (1997). Crystallographic structure of a helical lipopeptaibol antibiotic analogue. Lett. Peptide Sci. 4, 213-218.
9. E. Locardi, S. Mammi, E. Peggion, V. Monaco, F. Formaggio, M. Crisma, C. Toniolo and J. Kamphuis. Conformation of an analogue of the lipopeptaibol trichogin A IV containing the (xMe)Aun residue, in: Peptides 1996, R. Ramage and R. Epton, Eds, p. 591-592, Mayflower Scientific, Kingswinford, UK, 1998.
10. E. Locardi, S. Mammi, E. Peggion, V. Monaco, F. Formaggio, M. Crisma, C. Toniolo, B. Bodo, S. Rebuffat, J. Kamphuis and Q.B. Broxterman (1998). Conformation and membrane activity of an analogue of the peptaibol antibiotic trichogin GA IV with a lipophilic amino acid at the N-terminus. J. Peptide Sci., 4, 389-399.
11. V. Monaco, E. Locardi, F. Formaggio, M. Crisma, S. Mammi, E. Peggion, C. Toniolo, S. Rebuffat and B. Bodo (1998). Solution conformational analysis of amphiphilic helical, synthetic analogs of the lipopeptaibol trichogin GA IV. J. Peptide Res., in press.
12. x-tetrasubstituted α-amino acid. Bioorg. Med. Chem., in press.
13. C. Auvin-Guette, S. Rebuffat, I. Vuidepot, M. Massias and B. Bodo (1993). Structural elucidation of trikoningins KA and KB, peptalbols from Trichoderma koningti. J. Chem. Soc., Perkin Trans. 1, 249-255.
14. T. Fujita, S. Wada, A. Iida, T. Nishimura, M. Kanai and N. Toyama (1994). Fungal metabolites. XIII. Isolation and structural elucidation of new peptaibols, trichodecenins I and II, from Trichoderma viride. Chem. Pharm. Bull. 42, 489-492.
15. R. Gurunath and P. Balaram (1995). A nonhelical, multiple β-turn conformation in a glycine-rich heptapeptide fragment of trichogin GA IV containing a single central α-aminoisobutyric acid residue. Biopolymers 35, 21-29.
16. V. Monaco, F. Formaggio, M. Crisma, C. Toniolo, X. Shui and D.S. Eggleston (1996). Crystallographic structure of a multiple β-turn containing, glycine-rich heptapeptide: a synthetic precursor of the lipopeptaibol antibiotic trichodecenin I. Biopolymers 39, 31-42.
17. M. El-Hajji, S. Rebuffat, T. Le Doan, G. Klein, M. Satre and B. Bodo (1989). Interaction of trichorzianines A and B with model membranes and with the amoeba Dictyostalium. Biochim. Biophys. Acta 978, 97-104.
18. J.R. Vaughan, Jr. (1951). Acylalkylcarbonates as acylating agents for the synthesis of peptides. J. Am. Chem. Soc. 73, 35-47.
19. W.J. McGahren and M. Goodman (1967). Synthesis of peptide oxazolones and related compounds. Tetrahedron 23, 2017-2030.
20. G. Valle, F. Formaggio, M. Crisma, G.M. Bonora, C. Toniolo, A. Bavoso, E. Benedetti, B. Di Blasio, V. Pavone and C. Pedone (1986). Linear oligopeptides, Part 147. Chemical and crystallographic study of the reaction between benzyloxycarbonyl chloride and α-aminoisobutyric acid. J. Chem. Soc., Perkin Trans. 2, 1371-1376.
21. L.A. Carpino (1993). 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J. Am. Chem. Soc. 115, 4397-4398.
22. H.C. Brown and S. Narasimhan (1982). New powerful catalysts for the reduction of esters by lithium borohydride. J. Org. Chem. 47, 1604-1606.
23. E.V. Scriven (1983). 4-Dialkylaminopyridines: super acylation and alkylation catalysts. Chem. Soc. Rev. 12, 129-161.
24. 10-helix. Trends Biochem. Sci. 16, 350-353.
25. C. Toniolo, M. Crisma, F. Formaggio, G. Valle, G. Cavicchioni, G. Précigoux, A. Aubry and J. Kamphuis (1993). Structure of peptides from α-amino acids methylated at the α-carbon. Biopolymers 33, 1061-1072.
26. x-tetrasubstituted α-amino acid, is an excellent tool in material science and biochemistry. Biopolymers (Peptide Sci.) 47, 153-158.
27. M.S.P. Sansom (1991). The biophysics of peptide models of ion channels. Progr. Biophys. Mol. Biol. 55, 139-235.
28. R.M. Epand, Y. Shai, J.P. Segrest and G.M. Anantharamaiah (1995). Mechanisms for the modulation of membrane bilayer properties by amphipathic helical peptides. Biopolymers (Peptide Sci.) 37, 319-338.
29. C. Altenbach, D.A. Greenhalgh, H.G. Khorana and W.L. Hubbell (1994). A collision gradient method to determine the immersion depth of nitroxides in lipid bilayers. Application to spin labeled mutants of bacteriorhodopsin. Proc. Natl. Acad. Sci. USA 91, 1667-1671.
30. M. Barranger-Mathys and D.S. Cafiso (1996). Membrane structure of voltage-gated channel forming peptides by site-directed spin labeling. Biochemistry 35, 498-505.