Chemical modification of bacterial luciferase with ethoxyformic anhydride: evidence for an essential histidyl residue. 1976

J Cousineau, and E Meighen

Bacterial luciferase is a heteropolymeric protein (alphabeta) that catalyses the conversion of chemical energy to light by oxidation of a reduced flavin mononucleotide and a long chain aliphatic aldehyde. Elucidation of the specific amino acid residues involved in the enzymatic reaction is essential for understanding the mechanisms of the bioluminescent reaction. Luciferase has been found to be inactivated by ethoxyformic anhydride with a second-order rate constant of 146 M-1 min-1 at pH 6.1 and 0 degrees C with a concomitant increase in absorbance at 240 nm due to formation of ethoxyformylhistidyl derivatives. Activity could be restored by hydroxylamine and the pH curve of inactivation indicated the involvement of a residue having a pKa of 6.8. Both substrates, FMNH2 and aldehyde, protected the enzyme against inactivation, suggesting that the modification occurred at or near the active site. Incorporation of [14C]ethoxyformyl groups in luciferase indicated that inactivation resulted from the modification of about three histidyl residues, one histidine being found on the alpha subunit and two on the beta subunit. Hybridization experiments, in which ethoxyformylluciferase, alphambetam, was complemented with native subunits, alpha or beta, showed that the hybrid alphambetam, has the same activity as alphambetam whereas the activity of the hybrid alphabetam, was close to that of the reconstituted luciferase alphabeta. The results indicate that modification of only one histidyl residue on the alpha subunit inactivates luciferase and suggest that this histidyl residue plays an essential role in the mechanism of the bacterial bioluminescent reaction.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008156 Luciferases Enzymes that oxidize certain LUMINESCENT AGENTS to emit light (PHYSICAL LUMINESCENCE). The luciferases from different organisms have evolved differently so have different structures and substrates. Luciferase
D011485 Protein Binding The process in which substances, either endogenous or exogenous, bind to proteins, peptides, enzymes, protein precursors, or allied compounds. Specific protein-binding measures are often used as assays in diagnostic assessments. Plasma Protein Binding Capacity,Binding, Protein
D005019 Ethyl Ethers Organic compounds having ethyl groups bound to an oxygen atom. Ethoxy Compounds,Compounds, Ethoxy,Ethers, Ethyl
D005486 Flavin Mononucleotide A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues. FMN,Flavin Mononucleotide Disodium Salt,Flavin Mononucleotide Monosodium Salt,Flavin Mononucleotide Monosodium Salt, Dihydrate,Flavin Mononucleotide Sodium Salt,Riboflavin 5'-Monophosphate,Riboflavin 5'-Phosphate,Riboflavin Mononucleotide,Sodium Riboflavin Phosphate,5'-Monophosphate, Riboflavin,5'-Phosphate, Riboflavin,Mononucleotide, Flavin,Mononucleotide, Riboflavin,Phosphate, Sodium Riboflavin,Riboflavin 5' Monophosphate,Riboflavin 5' Phosphate,Riboflavin Phosphate, Sodium
D006639 Histidine An essential amino acid that is required for the production of HISTAMINE. Histidine, L-isomer,L-Histidine,Histidine, L isomer,L-isomer Histidine
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D000812 Anhydrides Chemical compounds derived from acids by the elimination of a molecule of water. Anhydride
D001419 Bacteria One of the three domains of life (the others being Eukarya and ARCHAEA), also called Eubacteria. They are unicellular prokaryotic microorganisms which generally possess rigid cell walls, multiply by cell division, and exhibit three principal forms: round or coccal, rodlike or bacillary, and spiral or spirochetal. Bacteria can be classified by their response to OXYGEN: aerobic, anaerobic, or facultatively anaerobic; by the mode by which they obtain their energy: chemotrophy (via chemical reaction) or PHOTOTROPHY (via light reaction); for chemotrophs by their source of chemical energy: CHEMOLITHOTROPHY (from inorganic compounds) or chemoorganotrophy (from organic compounds); and by their source for CARBON; NITROGEN; etc.; HETEROTROPHY (from organic sources) or AUTOTROPHY (from CARBON DIOXIDE). They can also be classified by whether or not they stain (based on the structure of their CELL WALLS) with CRYSTAL VIOLET dye: gram-negative or gram-positive. Eubacteria
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining

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