Tryptophan-14 is the preferred site of DBNBS spin trapping in the self-peroxidation reaction of sperm whale metmyoglobin with a single equivalent of hydrogen peroxide

Chemical Research in Toxicology
Michael R GuntherP R Ortiz de Montellano

Abstract

The 3,5-dibromo-4-nitrosobenzenesulfonate (DBNBS)-metmyoglobin adduct formed following the horse metmyoglobin-H(2)O(2) reaction has been assigned to both a tyrosyl and a tryptophanyl residue radical. At low H(2)O(2), hyperfine coupling to a (13)C atom in sperm whale metmyoglobin labeled at the tryptophan residues with (13)C allowed the unequivocal assignment of the primary adduct to a tryptophanyl radical. Trapping at Trp-14 of sperm whale myoglobin was indicated by greatly decreased electron paramagnetic resonance (EPR) spectral intensity of the DBNBS adducts of the Trp-14-Phe recombinant proteins. Complex EPR spectra with partially resolved hyperfine splittings from several atoms were obtained by pronase treatment of the DBNBS/*W14F metmyoglobin adducts. The EPR spectra of authentic DBNBS/*Tyr adducts were incubation time-dependent; the late time spectra resembled the spectra of pronase-treated DBNBS/*W14F sperm whale myoglobin adducts, suggesting formation of an unstable tyrosyl radical adduct in the latter proteins. When the H(2)O(2):metmyoglobin ratio was increased to 5:1, the EPR spectrum after pronase treatment supported trapping of a tyrosyl radical, although similar decreases in tryptophan content were detected at H(2)...Continue Reading

References

Jul 7, 1995·The Journal of Biological Chemistry·M R GuntherR P Mason
May 1, 1995·Biochemical Society Transactions·J A SilvesterM J Davies
Jan 24, 1997·The Journal of Biological Chemistry·J A DeGrayR P Mason
May 28, 1998·The Journal of Biological Chemistry·L J DeterdingK B Tomer
Dec 10, 1999·The Journal of Biological Chemistry·O M LardinoisP R Ortiz de Montellano
Apr 26, 2000·The Journal of Biological Chemistry·P K WittingA G Mauk
Mar 14, 2001·Biochimica Et Biophysica Acta·C L Hawkins, M J Davies
Apr 12, 2001·The Journal of Biological Chemistry·O M Lardinois, P R de Montellano
Jan 5, 2002·The Journal of Biological Chemistry·Michael R GuntherMeena K Sivaneri

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Citations

Apr 15, 2004·Free Radical Biology & Medicine·Michael J Davies, Clare L Hawkins
Nov 15, 2011·Bioelectrochemistry·Nadav Ben-Dov, Rafi Korenstein
Apr 9, 2009·Free Radical Biology & Medicine·Marilyn EhrenshaftRonald P Mason
May 12, 2004·Free Radical Biology & Medicine·Michael R Gunther
Apr 10, 2013·Biochimica Et Biophysica Acta·Clare L Hawkins, Michael J Davies
Jul 2, 2011·Biochimica Et Biophysica Acta·Michelle A YuGary J Gerfen
Feb 22, 2005·Biochimica Et Biophysica Acta·Dimitri A Svistunenko
Mar 31, 2016·The Biochemical Journal·Michael J Davies
Oct 7, 2008·Chemical Research in Toxicology·Magdalena A LamMichael J Davies
Nov 23, 2013·Energy & Fuels : an American Chemical Society Journal·Zofia MaskosBarry Dellinger

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