PMID: 8589069Jan 1, 1995Paper

Arylhydrazines as probes of hemoprotein structure and function

Biochimie
P R Ortiz de Montellano

Abstract

The reactions of arylhydrazines (ArNHNH2) or aryldiazenes (ArN = NH) with simple iron porphyrins or with hemoproteins that have relatively open active sites, including hemoglobin, myoglobin, cytochrome P450, chloroperoxidase, catalase, prostaglandin synthase, and indoleamine-2,3-dioxygenase yield sigma-bonded aryl-iron complexes. Denaturation of the protein complexes under aerobic, acidic conditions shifts the aryl group to the porphyrin nitrogens and produces mixtures of the four possible N-arylprotoporphyrin IX regioisomers. The regioisomers are obtained in approximately equal amounts if the iron-to-nitrogen shift occurs outside of the protein but the ratio of isomers differs if the rearrangement is controlled by the protein. Only in the case of cytochrome P450 enzymes can the shift be induced to occur without denaturation of the protein. The isomer ratios obtained when the shift occurs in the intact active site provide direct experimental information on the active site topology and dynamics. Topological information has thus been obtained for cytochromes P450 1A1, 1A2, 2B1, 2B2, 2B4, 2B10, 2B11, 2E1, 11A1, 51, 101, 102, and 108. In contrast to hemoproteins with open active sites, conventional peroxidases react with arylhydraz...Continue Reading

References

Jun 1, 1977·Proceedings of the National Academy of Sciences of the United States of America·H A ItanoT S Vedvick
Jul 1, 1990·Archives of Biochemistry and Biophysics·G D DePillisP R Ortiz de Montellano
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Citations

Jul 7, 2001·Free Radical Biology & Medicine·P R GardnerA M Gardner
Jan 26, 2007·Journal of the American Chemical Society·Grzegorz Wojciechowski, Paul R Ortiz de Montellano
Oct 20, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Radu Silaghi-Dumitrescu, Chris E Cooper
Jan 3, 1997·Biochemical and Biophysical Research Communications·Y J ChunF P Guengerich
Feb 10, 2006·Archives of Biochemistry and Biophysics·Robert A B van WaterschootRichard A Tschirret-Guth
Sep 6, 2005·Biochemical and Biophysical Research Communications·Clinton R Nishida, Paul R Ortiz de Montellano
Dec 18, 2009·Journal of the American Chemical Society·Alexander LaskavyRonny Neumann
Oct 1, 2016·Journal of Inorganic Biochemistry·Bing WangGeorge B Richter-Addo
Nov 4, 2004·Journal of Molecular Biology·Anna-Maria A HaysDavid B Goodin
Mar 7, 1997·The Journal of Biological Chemistry·N C GerberP R Ortiz de Montellano
Aug 29, 1998·The Journal of Biological Chemistry·E A DierksP R de Montellano
May 9, 2000·The Journal of Biological Chemistry·L S KooP R Ortiz de Montellano
Jun 12, 2003·Chemical Reviews·Christophe Colas, Paul R Ortiz de Montellano

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