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Papers In Press, published online ahead of print July 31, 2001
J. Biol. Chem, 10.1074/jbc.C100371200
Submitted on July 2, 2001
Revised on July 31, 2001
Accepted on July 30, 2001
Institute for Molecular Science, Okazaki, Aichi 444-8585
Corresponding Author: yoshi{at}ims.ac.jp
The F43W/H64L Mb mutant was previously constructed to investigate the effects of electron-rich tryptophan residue in the heme vicinity on the catalysis, where we found that Trp-43 in the mutant was oxidatively modified in the reaction with m-chloroperbenzoic acid (mCPBA). To identify the exact structure of the modified tryptophan in this study, the mCPBA-treated F43W/H64L mutant has been digested stepwise with Lys-C achromobacter and trypsin to isolate two oxidation products by preparative FPLC. The close examinations of the 1H NMR spectra of peptide fragments reveal that two forms of the modified tryptophan must have 2,6-disubstituted indole substructures. The 13C NMR analysis suggests that one of the modified tryptophan bears a unique hydroxyl group in stead of the NH2 group at the amino-terminal. The results together with Ms/Ms analysis (30 Da increase in mass of Trp-43) indicate that oxidation products of Trp-43 are 2,6-dihydro-2,6-dioxoindole and 2,6-dihydro-2-imino-6-oxoindole derivatives. Our finding is the first example of the oxidation of aromatic carbons by the myoglobin mutant system.
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