A left-handed α-helix containing both L- and D-amino acids: The solution structure of the antimicrobial lipodepsipeptide tolaasin

Proteins: Structure, Function and Genetics

Volumn 52, Issue 4, 2003, Pages 534-543

  Jourdan, Fabrice ^a   Lazzaroni, Silvia ^b   Méndez, Blanca López ^a   Lo Cantore, Pietro ^c   De Julio, Marianna ^a   Amodeo, Pietro ^a   Iacobellis, Nicola S ^c   Evidente, Antonio ^b   Motta, Andrea ^a  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF BASILICATA   (Italy)

Author keywords

Agaricus bisporus; Amphipathic helix; Antibiotic substances; Molecular dynamics; NMR; Pseudomonas tolaasii; SDS

Indexed keywords

ANTIINFECTIVE AGENT; DODECYL SULFATE SODIUM; LACTONE; LIPODEPSIPEPTIDE; MACROCYCLIC COMPOUND; PROLINE; THREONINE; TOLAASIN; UNCLASSIFIED DRUG;

ALPHA HELIX; AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ANTIGENICITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL COLONIZATION; BACTERIAL VIRULENCE; CARBOXY TERMINAL SEQUENCE; CYTOLYSIS; DRUG DESIGN; ENZYME DEGRADATION; MOLECULAR DYNAMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; PSEUDOMONAS; PSEUDOMONAS TOLAASII; SIMULATION; STRAIN DIFFERENCE;

AMINO ACIDS; BACTERIAL PROTEINS; BACTERIAL TOXINS; COMPUTER SIMULATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; SOLUTIONS; THERMODYNAMICS;

AGARICUS; AGARICUS BISPORUS; BACTERIA (MICROORGANISMS); BASIDIOMYCOTA; PSEUDOMONAS; PSEUDOMONAS TOLAASII;

EID: 0042420680     PISSN: 08873585     EISSN: None     Source Type: Journal    
DOI: 10.1002/prot.10418     Document Type: Article

References (55)

1. Segrest JP, DeLoof H, Dohlman JG, Brouillette CG, Anantharamaiah GM. Amphipathic helix motif: classes and properties. Proteins 1990;8:103-117.
2. Westerhoff HV, Juretic D, Hendler RW, Zasloff M. Magainins and the disruption of membrane-linked free-energy transduction. Proc Natl Acad Sci USA 1989;87:6597-6601.
3. Ojcius DM, Young JDE. Cytolytic pore-forming proteins and peptides: is there a common structural motif? Trends Biochem Sci 1991;16:225-229.
4. Shai Y. Molecular recognition between membrane-spanning polypeptides. Trends Biochem Sci 1995;20:460-464.
5. Wade D, Boman A, Wåhlin B, Andreu D, Boman HG, Merrifield RB. All-D amino acid-containing channel-forming antibiotic peptides. Proc Natl Acad Sci USA 1990;87:4761-4765.
6. Benkirane N, Friede M, Guichard G, Briand JP, Van RM, Muller S. Antigenicity and immunogenicity of modified synthetic peptides containing D- amino acid residues. Antibodies to a D- enantiomer do recognise the parent L-hexapeptide and reciprocally. J Biol Chem 1993;268:26279-26285.
7. Shai Y, Oren Z. Diastereoisomers of cytolysins, a novel class of potent antibacterial peptides. J Biol Chem 1996;271:7305-7308.
8. Oren Z, Shai Y. Selective lysis of bacteria but not mammalian cells by diastereomers of melittin: structure-function study. Biochemistry 1997;36:1826-1835.
9. Bender CL, Alarcón-Chaidez F, Gross DC. Pseudomonas syringae phytotoxins: mode of action, regulation, and biosynthesis by peptide and polyketide synthetases. Microbiol Mol Biol Rev 1999;63:266-292.
10. Ballio A, Barra D, Bossa F, Collina A, Grgurina I, Marino G, Moneti G, Paci M, Pucci P, Segre A, Simmaco M. Syringopeptins, new phytotoxic lipodepsipeptides of Pseudomonas syringae pv. syringae. FEBS Lett 1991;291:109-112.
11. Raney PB, Brodey CL, Johnstone K. Biology of Pseudomonas tolaasii, cause of brown blotch disease of the cultivated mushroom. Adv Plant Pathol 1992;8:95-117.
12. Tolaas AG. A bacterial disease of cultivated mushroom. Phytopathology 1915;5:51-54.
13. Nutkins JC, Mortishire-Smith RJ, Packman LC, Brodey CL, Rainey PB, Johnstone K, Williams DH. Structure determination of tolaasin, an extracellular lipodepsipeptide produced by the mushroom pathogen Pseudomonas tolaasii Paine. J Am Chem Soc 1991;113:2621-2627.
14. Brodey CL, Rainey PB, Tester M, Johnstone K. Bacterial blotch disease of the cultivated mushroom is caused by an ion-channel forming lipodepsipeptide toxin. Mol Plant Microbe Interact 1991;4:407-411.
15. Fox RO, Richards FM. A voltage-gated ion channel model inferred from the crystal structure of alamethicin at 1.5-Å resolution. Nature 1982;300:325-330.
16. Sansom MSP. Structure and function of channel-forming peptaibols. Q Rev Biophys 1993;26:365-421.
17. Cafiso DS. Alamethicin: a peptide model for voltage gating and protein-membrane interactions. Ann Rev Biophys Biomol Struct 1994;23:141-165.
18. Raney PB, Brodey CL, Johnstone K. Biological properties and spectrum of activity of tolaasin, a lipodepsipeptide toxin produced by the mushroom pathogen Pseudomonas tolaasii. Physiol Mol Plant Pathol 1991;39:57-70.
19. DeGrado WF, Wasserman ZR, Lear JD. Protein design, a minimalist approach. Science 1989;243:622-628.
20. Bechinger B, Zasloff M, Opella SJ. Structure and orientation of the antibiotic peptide magainin in membranes by solid-state nuclear magnetic resonance spectroscopy. Protein Sci 1993;2:2077-2084.
21. Sewhyzer R. Molecular mechanism of opioid receptor selection. Biochemistry 1986;25:6335-6342.
22. Mortishire-Smith RJ, Drake AF, Nutkins JC, Williams DH. Left handed alpha-helix formation by a bacterial peptide. FEBS Lett 1991;278:244-246.
23. King EO, Ward MK, Raney DE. Two simple media for the demonstration of pyocyanin and fluorescein. J Lab Clin Med 1954;44:301-307.
24. Iacobellis NS, Lavermicocca P, Grgurina I, Simmaco M, Ballio A. Phytotoxic properties of Pseudomonas syringae pv. Syringae toxins. Physiol Mol Plant Pathol 1992;40:107-116.
25. Lavermicocca P, Iacobellis NS, Simmaco M, Graniti A. Biological properties and spectrum of activity of Pseudomonas syringae pv. syringae toxins. Physiol Mol Plant Pathol 1997;50:129-140.
26. Peng JT. Resistance to disease in A. bisporus (Lange) Imbach. Ph.D. Thesis, University of Leeds, Department of Plant Science; 1996.
27. Jeener J, Meier BH, Bachmann P, Ernst RR. Investigation of exchange processes by two-dimensional NMR spectroscopy. J Chem Phys. 1976;71:4546-4553.
28. Braunschweiler L., Ernst RR. Coherence transfer by isotropic mixing: application of proton correlation spectroscopy. J Magn Reson 1983;53:521-528.
29. Drobny G, Pines A, Sinton S, Weitkamp D, Wemmer D. Fourier transform multiple quantum nuclear magnetic resonance. Faraday Div Chem Soc Symp 1979;13:49-55.
30. Piotto M, Saudek V, Sklenar V. Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions. J Biomol NMR 1992;2:661-666.
31. Griesinger C, Otting G, Wüthrich K, Ernst RR. Clean TOCSY for 1H spin system identification in macromolecules. J Am Chem Soc 1988;110:7870-7872.
32. Bax A, Davis DG. MLEV-17-based two-dimensional homonuclear magnetisation transfer spectroscopy. J Magn Reson 1985;65:355-366.
33. Pearlman DA, Case DA, Caldwell JW, Ross WS, Cheatman III TE, DeBolt S, Ferguson D, Seibel G, Kollman P. AMBER, a package of computer programs for applying molecular mechanics, normal mode analysis, molecular dynamics and free energy calculations to simulate the structural and energetic properties of molecules. Comp Phys Commun 1995;91:1-41.
34. Wüthrich K, Billeter M, Braun W. Pseudo-structures for the 20 common amino acids for use in studies of protein conformations by measurements of intramolecular proton-proton distance constraints with nuclear magnetic resonance. J Mol Biol 1983;169:949-961.
35. Wüthrich K. NMR in proteins and nucleic acids. New York: John Wiley & Sons; 1986.
36. Weiner SJ, Kollman PA, Case DA, Singh UC, Ghio C, Alagona G, Profeta S Jr, Weiner PA. A new force field for molecular mechanical simulation of nucleic acids and proteins. J Am Chem Soc 1981;106:765-784.
37. Weiner PK, Kollman PA, Nguyen DT, Case DA. An all-atom force-field for molecular mechanical simulation of nucleic acids and proteins. J Comput Chem 1986;7:230-252.
38. Berendsen HJC, Postma JPM, van Gunsteren WF, Di Nola A, Haak JM. Molecular dynamics with coupling to an external bath. J Chem Phys 1984;81:3684-3690.
39. Ryckaert JP, Ciccotti G, Berendsen HJC. Numerical integration of the Cartesian equations of motions of a system with constraints: molecular dynamics of n-alcanes. J Comp Phys 1977;23:327-341.
40. Case DA, Pearlman DA, Caldwell JW, Cheatham III TE, Wang J, Ross, WS, Simmerling CL, Darden TA, Merz KM, Stanton RV, Cheng AL, Vicent JJ, Crowley M, Tsui V, Gohlke H., Radmer RJ, Duan Y, Pitera J, Massova I, Seibel GL, Singh UC, Weiner PK, Kollman PA. AMBER 7, University of California, San Francisco. 2002.
41. Darden T, York D, Pedersen L. Particle mesh Ewald - an Nlog(N) method for Ewald sums in large systems. J Chem Phys 1993;98:10089-10092.
42. Essmann U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG. A smooth particle mesh Ewald method. J Chem Phys 1995;103:8577-8593.
43. Tsui V, Case DA. Molecular dynamics simulations of nucleic acids with a generalized Born Solvation model. J Am Chem Soc 2000;122:2489-2498.
44. Koradi R, Billeter M, Wüthrich K. MOLMOL: a program for display and analysis of macromolecular structures. J Mol Graph 1996;14:51-55.
45. Wagner G, Neuhaus D, Wörgötter E, Vasák M, Kägi JRH, Wüthrich K. Nuclear magnetic resonance identification of "half-turn" and 3(10)-helix secondary structure in rabbit liver metallothionein-2. J Mol Biol 1986;187:131-135.
46. Dyson HJ, Rance M, Houghten RA, Wright PE, Lerner RA. Folding of immunogenic peptide fragments of proteins in water solution. II. The nascent helix. J Mol Biol 1988;201:201-217.
47. Ballio A, Bossa F, Di Giorgio A, Di Nola C, Manetti M, Paci M, Scaloni A, Segre A. Solution conformation of the Pseudomonas syringae pv. syringae phytotoxic lipodepsipeptide syringopeptin 25-A. Two-dimensional NMR, distance geometry and molecular dynamics. Eur J Biochem 1995;234;747-758.
48. Storm DR, Rosenthal KS, Swanson PE. Polymyxin and related peptide antibiotics. Annu Rev Biochem 1977;46:723-763.
49. Clark DP, Durell S, Maloy W, Zasloff M. Ranalexin. A novel antimicrobial peptide from bullfrog (Rana catesbeiana) skin, structurally related to the bacterial antibiotic, polymyxin. J Biol Chem 1994;269:10849-10855.
50. Simmaco M, Mignogna G, Barra D, Bossa F. Antimicrobial peptides from skin secretions of Rana esculenta. Molecular cloning of cDNAs encoding esculentin and brevinins and isolation of new active peptides. J Biol Chem 1994;269:11956-11961.
51. Oren Z, Shai Y. Mode of action of linear amphipathic alpha-helical antimicrobial peptides. Biopolymers 1998;47:451-463.
52. Andreu D, Rivas L. Animal antimicrobial peptides: an overview. Biopolymers 1998;47:415-433.
53. Hutchison ML, Johnstone K. Evidence for the involvement of the surface active properties of the extracellular toxin tolaasin in the manifestation of brown blotch disease symptoms by Pseudomonas tolaasii on Agarus bisporus. Physiol Mol Plant Pathol 1993;42:373-384.
54. Soler-Rivas C, Jolivet S, Arpin N, Oliver JM, Wichers HJ. Biochemical and physiological aspects of brown blotch disease of Agaricus bisporus. FEMS Microbiol Rev 1999;23:591-614.
55. Moquet F, Mamoun M, Olivier JM. Pseudomonas tolaasii and tolaasin: comparison of symptom induction on a wide range of Agaricus bisporus strains. FEMS Microbiol Lett 1996;142:99-103.