title: Comparison of the effects of ozone on the modification of amino acid residues in glutamine synthetase and bovine serum albumin.
abstract: During exposure to ozone, the methionine and aromatic amino acid residues of Escherichia coli glutamine synthetase (GS) and bovine serum albumin (BSA) are oxidized rapidly in the order Met > Trp > Tyr approximately His > Phe. The loss of His is matched by a nearly equivalent formation of aspartate or of a derivative that is converted to aspartic acid upon acid hydrolysis. Conversion of His to aspartate was confirmed by showing that the oxidation of E. coli protein in which all His residues were uniformly labeled with 14C gave rise to 14C-labeled aspartic acid in 80% yield and also by the demonstration that His residues in the tripeptides Ala-His-Ala or Ala-Ala-His gave rise to nearly stoichiometric amounts of aspartic acid whereas oxidation of His-Ala-Ala yielded only 36% aspartate. The oxidation of BSA and GS led to formation, respectively, of 11 and 3.3 eq of carbonyl groups and 0.5 and 0.3 eq of quinoprotein per subunit. Although BSA and GS contain nearly identical amounts of each kind of aromatic amino acid residues, oxidation of these residues in BSA was about 1.5-2.0 times faster than in GS indicating that the susceptibility to oxidation is dependent on the primary, secondary, tertiary, and quaternary structure of the protein.
authors.affiliation: Laboratory of Biochemistry, NHLBI, National Institutes of Health, Bethesda, Maryland 20892-0342, USA.
authors.forename: B S
authors.initials: BS
authors.lastname: Berlett
authors.forename: R L
authors.initials: RL
authors.lastname: Levine
authors.forename: E R
authors.initials: ER
authors.lastname: Stadtman
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids; D000818:Animals; D002417:Cattle; D004926:Escherichia coli / Q000201:enzymology; D005974:Glutamate-Ammonia Ligase / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism; D006639:Histidine; D007700:Kinetics; D008715:Methionine; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000737:chemistry; D010084:Oxidation-Reduction; D010126:Ozone / Q000494:pharmacology*; D010649:Phenylalanine; D012710:Serum Albumin, Bovine / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism; D013329:Structure-Activity Relationship; D014364:Tryptophan; D014443:Tyrosine
chemical_list: D000596:Amino Acids; D009842:Oligopeptides; D012710:Serum Albumin, Bovine; D014443:Tyrosine; D010649:Phenylalanine; D006639:Histidine; D010126:Ozone; D014364:Tryptophan; D008715:Methionine; D005974:Glutamate-Ammonia Ligase