Flash photolysis of cutinase: Identification and decay kinetics of transient intermediates formed upon UV excitation of aromatic residues

Biophysical Journal

Volumn 97, Issue 1, 2009, Pages 211-226

  Neves Petersen, Maria Teresa ^a   Klitgaard, Søren ^a   Pascher, Torbjorn ^b   Skovsen, Esben ^a   Polivka, Tomas ^c   Yartsev, Arkady ^b   Sundström, Villly ^b   Petersen, Steffen B ^a,d  

^a AALBORG UNIVERSITY   (Denmark)

^b LUND UNIVERSITY   (Sweden)

^c UNIVERSITY OF SOUTH BOHEMIA   (Czech Republic)

^d UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; CUTINASE; LYSOZYME; TRYPTOPHAN;

ARTICLE; CONTROLLED STUDY; DISULFIDE BOND; ELECTRICITY; ELECTRON TRANSPORT; FUSARIUM SOLANI; HYDROGEN BOND; NONHUMAN; PH MEASUREMENT; PHOTOLYSIS; PROTEIN STRUCTURE; SOLVATION; ULTRAVIOLET RADIATION;

FUSARIUM SOLANI;

CARBOXYLIC ESTER HYDROLASES; ELECTRONS; FUNGAL PROTEINS; FUSARIUM; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, MOLECULAR; MURAMIDASE; PHOTOLYSIS; SPECTRUM ANALYSIS; TRYPTOPHAN; ULTRAVIOLET RAYS;

EID: 68949118397     PISSN: 00063495     EISSN: 15420086     Source Type: Journal    
DOI: 10.1016/j.bpj.2009.01.065     Document Type: Article

References (50)

1. Bent, D. V., and E. Hayon. 1975. Excited-state chemistry of aromatic amino-acids and related peptides .3. tryptophan. J. Am. Chem. Soc. 97:2612-2619.
2. Creed, D. 1984. The photophysics and photochemistry of the near-UV absorbing amino-acids .1. Tryptophan and its simple derivatives. Photochem. Photobiol. 39:537-562.
3. Bent, D. V., and E. Hayon. 1975. Excited-state chemistry of aromatic amino-acids and related peptides .1.tyrosine. J. Am. Chem. Soc. 97:2599-2606.
4. Creed, D. 1984. The photophysics and photochemistry of the near-uv absorbing amino-acids .2. Tyrosine and its simple derivatives. Photochem. Photobiol. 39:563-575.
5. Bent, D. V., and E. Hayon. 1975. Excited-state chemistry of aromatic amino-acids and related peptides .2.phenylalanine. J. Am. Chem. Soc. 97:2606-2612.
6. Creed, D. 1984. The photophysics and photochemistry of the near-UV absorbing amino-acids.3. Cystine and its simple derivatives. Photochem. Photobiol. 39:577-583.
7. Hart, E. J., and J. W. Boag. 1962. Absorption spectrum of the hydrated electron in water and in aqueous solutions. J. Am. Chem. Soc. 84:4090-4095.
8. Wiesenfeld, J. M., and E. P. Ippen. 1980. Dynamics of electron solvation in liquid water. Chem. Phys. Lett. 73:47-50.
9. Crowell, R. A., and D. M. Bartels. 1996. Multiphoton ionization of liquid water with 3.0-5.0 eV photons. J. Phys. Chem. 100:17940-17949.
10. Sander, M. U., K. Luther, and J. Troe. 1993. On the photoionization mechanism of liquid water. Ber. Bunsenges. Phys. Chem. 97:953-961.
11. Migus, A., Y. Gauduel, J. L. Martin, and A. Antonetti. 1987. Excess electrons in liquid water: first evidence of a prehydrated state with femtosecond lifetime. Phys. Rev. Lett. 58:1559-1562.
12. Long, F. H., H. Lu, and K. B. Eisenthal. 1990. Femtosecond studies of the presolvated electrons: an excited state of the solvated electron? Phys. Rev. Lett. 64:1469-1472.
13. Tsentalovich, Y. P., O. A. Snytnikova, and R. Z. Sagdeev. 2004. Properties of excited states of aqueous tryptophan. Photochem. Photobiol. Chem. 162:371-379.
14. Armstrong, R. C., and A. J. Swallow. 1969. Pulse- and gamma-radiolysis of aqueous solutions of tryptophan. Radiat. Res. 40:563-579.
15. Hoffman, M. Z., and E. Hayon. 1972. One-electron reduction of the disulfide linkage in aqueous solution. Formation, protonation, and decay kinetics of the RSSR- radical. J. Am. Chem. Soc. 94:7950-7957.
16. Adams, G. E., R. L. Willson, J. E. Aldrich, and R. B. Cundall. 1969. On the mechanism of the radiation-induced inactivation of lysozyme in dilute aqueous solution. Int. J. Radiat. Biol. 16:333-342.
17. Redpath, J. L., R. Santus, J. Ovadia, and L. I. Grossweiner. 1975. Oxidation of tryptophan by radical-anions. Int. J. Radiat. Biol. 27:201-204.
18. Grossweiner, L. I., and Y. Usui. 1971. Flash photolysis and inactivation of aqueous lysozyme. Photochem. Photobiol. 13:195-214.
19. Li, Z., W. E. Lee, and W. C. Galley. 1989. Distance dependence of the tryptophan-disulfide interaction at the triplet level from pulsed phosphorescence studies on a model system. Biophys. J. 56:361-367.
20. Neves-Petersen, M. T., Z. Gryczynski, J. Lakowicz, P. Fojan, S. Pedersen, et al. 2002. High probability of disrupting a disulphide bridge mediated by an endogenous excited tryptophan residue. Protein Sci. 11:588-600.
21. Neves-Petersen, M. T., T. Snabe, S. Klitgaard, M. Duroux, and S. B. Petersen. 2006. Photonic activation of disulfide bridges achieves oriented protein immobilization on biosensor surfaces. Protein Sci. 15:343-351.
22. Prompers, J. J., C. W. Hilbers, and H. A. M. Perpermans. 1999. Tryptophan mediated photoreduction of disulfide bond causes unusual fluorescence behaviour of Fusarium solani pisi cutinase. FEBS Lett. 45:409-416.
23. Vanhooren, A., B. Devreese, K. Vanhee, J. Van Beeumen, and I. A. Hanssens. 2002. Photoexcitation of tryptophan groups induces reduction of two disulfide bonds in goat alpha-lactalbumin. Biochemistry. 41:11035-11043.
24. Duroux, M., E. Skovsen, M. T. Neves-Petersen, L. Duroux, L. Gurevich, et al. 2007. Light-induced immobilisation of biomolecules as a replacement for present nano/micro droplet dispensing based arraying technologies. Proteomics. 7:3491-3499.
25. Neves-Petersen, M. T., M. Duroux, E. Skovsen, L. Duroux, and S. B. Petersen. 2009. Printing novel architectures of nanosized molecules with micrometer resolution using light. J. Nanosci. Nanotech. 9:3372-3381.
26. Skovsen, E., M. T. Neves-Petersen, A. Kold, L. Duroux, and S. B. Petersen. 2009. Immobilizing biomolecules near the diffraction limit. J. Nanosci. Nanotech. 9:4333-4337.
27. Kerwin, B. A., and R. L. Remmele, Jr. 2007. Protect from light: photodegradation and protein biologics. J. Pharm. Sci. 96:1468-1479.
28. Neves-Petersen, M. T., and S. B. Petersen. 2003. Protein electrostatics: a review of the equations and methods used to model electrostatic equations in biomolecules-applications in biotechnology. Biotechnol. Annu. Rev. 9:315-395.
29. Neves-Petersen, M. T., E. I. Petersen, P. Fojan, M. Noronha, R. G. Madsen, et al. 2001. Engineering the pH-optimum of a triglyceride lipase: from predictions based on electrostatic computations to experimental results. J. Biotechnol. 87:225-254.
30. Janssens, L. D., N. Boens, M. Ameloot, and F. C. De Schryver. 1990. A systematic study of the global analysis of multiexponential fluorescence decay surfaces using reference convolution. J. Phys. Chem. 94: 3564-3576.
31. Verveer, P. J., A. Squire, and P. I. Bastiaens. 2000. Global analysis of fluorescence lifetime imaging microscopy data. Biophys. J. 78:2127-2137.
32. Kloepfer, J. A., V. H. Vilchiz, V. A. Lenchenkov, A. C. Germaine, and S. E. Bradforth. 2000. The ejection distribution of solvated electrons generated by the one-photon photodetachment of aqueous I- and twophoton ionization of the solvent. J. Chem. Phys. 113:6288-6307.
33. Mazul, V. M., D. G. Scherbin, V. A. Shashilov, A. A. Sukhodola, E. M. Zaitseva, et al. 2003. Recombination prolonged luminescence of indole and tryptophan in a solution at room temperature. J. Appl. Spectrosc. 70:270-274.
34. Burdi, D., B. M. Aveline, P. D. Wood, J. Stubbe, and R. W. Redmond. 1997. Generation of a tryptophan radical in high quantum yield from a novel amino acid analog using near-UV/visible light. J. Am. Chem. Soc. 119:6457-6460.
35. Grossweiner, L. I., G. W. Swenson, and E. F. Zwicker. 1963. Photochemical generation of the hydrated electron. Science. 141:805-806.
36. Grossweiner, L. I., A. G. Kaluskar, and J. F. Baugher. 1976. Flash photolysis of enzymes. Int. J. Radiat. Biol. 29:1-16.
37. Bonifacic, M., and K.-D. Asmus. 1984. Adduct formation and absolute rate constants in the displacement reaction of thiyl radicals with disul-fides. J. Phys. Chem. 88:6286-6290.
38. Morine, G. H., and R. R. Kuntz. 1981. Observations of c-s and s-s bond cleavage in the photolysis of disulfides in solution. Photochem. Photobiol. 33:1-5.
39. Purdie, J. W., H. A. Gillis, and N. V. Klassen. 1973. The pulse radiolysis of penicillamine and penicillamine disulfide in aqueous solution. Can. J. Chem. 51:3132-3142.
40. Neta, P., and R. H. Schuler. 1971. Rate constants for reaction of hydrogen atoms with compounds of biochemical interest. Radiat. Res. 47:612-627.
41. Ito, O., and M. Matsuda. 1978. Flash photolysis study on the addition reaction of alkylthiyl radical to olefins. Bull. Chem. Soc. Jpn. 51:427-430.
42. Grossweiner, L. I., and Y. Usui. 1970. The role of the hydrated electron in photoreduction of cystine in the presence of indole. Photochem. Photobiol. 11:53-56.
43. Spanel, P., and D. Smith. 1995. Recent studies of electron attachment and electron-ion recombination at thermal energies. Plasma Sources Sci. Technol. 4:302-306.
44. Faraggi, M., and A. Bettelheim. 1977. The reaction of the hydrated electron with amino acids, peptides, and proteins in aqueous solutions: tryptophyl peptides. Radiat. Res. 72:81-88.
45. Jovanovic, S. V., and S. J. Steenken. 1992. Substituent effects on the spectral, acid-base, and redox properties of indolyl radicals: a pulse radiolysis study. J. Phys. Chem. 96:6674-6679.
46. Dudley Bryant, F., R. Santus, and L. I. Grossweiner. 1975. Laser flash photolysis of aqueous tryptophan. J. Phys. Chem. 79:2711-2716.
47. Feitelson, J., and E. Hayon. 1973. Electron ejection and electron capture by phenolic compounds. J. Phys. Chem. 77:10-15.
48. Feitelson, J., and E. Hayon. 1973. Electron transfer from the excited state of tyrosine to compounds containing disulfide linkages. Photochem. Photobiol. 17:265-274.
49. Bansal, K. M., and R. W. Fessenden. 1976. Pulse radiolysis studies of the oxidation of phenols by s04- and br2- in aqueous solutions' 2. Rad. Res. 67:1-8.
50. Fielden, E. M., and E. J. Hart. 1967. Primary radical yields in pulse-irradiated alkaline aqueous solution. Radiat. Res. 32:564-580.