Insights into the catalytic mechanism of tyrosine phenol-lyase from X-ray structures of quinonoid intermediates.

The Journal of Biological Chemistry
Dalibor MilićAlfred A Antson

Abstract

Amino acid transformations catalyzed by a number of pyridoxal 5'-phosphate (PLP)-dependent enzymes involve abstraction of the Calpha proton from an external aldimine formed between a substrate and the cofactor leading to the formation of a quinonoid intermediate. Despite the key role played by the quinonoid intermediates in the catalysis by PLP-dependent enzymes, limited accurate information is available about their structures. We trapped the quinonoid intermediates of Citrobacter freundii tyrosine phenol-lyase with L-alanine and L-methionine in the crystalline state and determined their structures at 1.9- and 1.95-A resolution, respectively, by cryo-crystallography. The data reveal a network of protein-PLP-substrate interactions that stabilize the planar geometry of the quinonoid intermediate. In both structures the protein subunits are found in two conformations, open and closed, uncovering the mechanism by which binding of the substrate and restructuring of the active site during its closure protect the quinonoid intermediate from the solvent and bring catalytically important residues into positions suitable for the abstraction of phenol during the beta-elimination of L-tyrosine. In addition, the structural data indicate a m...Continue Reading

References

Jan 1, 1975·Advances in Applied Microbiology·H Yamada, H Kumagai
Nov 1, 1988·European Journal of Biochemistry·N G FaleevV M Belikov
Apr 1, 1987·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·M M PalcicH G Floss
Jul 1, 1987·Archives of Biochemistry and Biophysics·R S Phillips
Nov 1, 1988·European Journal of Biochemistry·P AdriaensensJ Gelan
Dec 30, 1987·European Journal of Biochemistry·T V DemidkinaA V Azhayev
Feb 7, 1969·Biochemical and Biophysical Research Communications·H KumagaiH Fukami
Jan 31, 1972·Biochemical and Biophysical Research Communications·H YamadaS Okumura
Jun 5, 1970·Biochemical and Biophysical Research Communications·H KumagaiH Yamada
Apr 15, 1984·Journal of Molecular Biology·J F KirschP Christen
Apr 27, 1993·Biochemistry·A A AntsonK S Wilson
Jan 9, 1999·The Journal of Biological Chemistry·B MouratouP Christen
May 20, 1999·Nature Structural Biology·A PerrakisV S Lamzin
Nov 18, 2000·European Journal of Biochemistry·N G FaleevR M Khomutov
Jan 3, 2001·Acta Crystallographica. Section D, Biological Crystallography·M D WinnG N Murshudov
Apr 6, 2002·The Journal of Biological Chemistry·Robert S PhillipsAndrea Mozzarelli
Apr 11, 2003·Biochimica Et Biophysica Acta·Robert S PhillipsNicolai G Faleev
Oct 9, 2003·Doklady. Biochemistry and Biophysics·A I PapisovaT V Demidkina
Sep 1, 1994·Acta Crystallographica. Section D, Biological Crystallography·UNKNOWN Collaborative Computational Project, Number 4
May 1, 1997·Acta Crystallographica. Section D, Biological Crystallography·G N MurshudovE J Dodson
Dec 2, 2004·Acta Crystallographica. Section D, Biological Crystallography·Paul Emsley, Kevin Cowtan
Apr 25, 2007·Nucleic Acids Research·Ian W DavisDavid C Richardson
Aug 8, 2007·Journal of Molecular Biology·Evgeny Krissinel, Kim Henrick
Mar 21, 2008·Chembiochem : a European Journal of Chemical Biology·Thomas R M BarendsIlme Schlichting
Jan 1, 1997·Methods in Enzymology·Zbyszek Otwinowski, Wladek Minor

❮ Previous
Next ❯

Citations

Nov 18, 2010·Proceedings of the National Academy of Sciences of the United States of America·Markos KoutmosRuma Banerjee
May 12, 2009·Molekuliarnaia biologiia·T V DemidkinaL N Zakomyrdina
Oct 10, 2013·BioMed Research International·Alessandra AstegnoPaola Dominici
Jun 8, 2012·Proteins·Yuichiro KezukaTakamasa Nonaka
Dec 21, 2011·Journal of Enzyme Inhibition and Medicinal Chemistry·Ratna SinghAndrea Mozzarelli
May 28, 2016·Amino Acids·Quang DoRobert S Phillips
Aug 8, 2018·Acta Crystallographica. Section D, Structural Biology·Robert S PhillipsZachary A Wood
Apr 3, 2020·Applied Biochemistry and Biotechnology·Hang-Qin ZhuYu-Guo Zheng
Aug 2, 2020·Journal of Industrial Microbiology & Biotechnology·Hongmei HanJingwen Zhou
Sep 9, 2011·Journal of the American Chemical Society·Dalibor MilićAlfred A Antson

❮ Previous
Next ❯

Related Concepts

Related Feeds

ASBMB Publications

The American Society for Biochemistry and Molecular Biology (ASBMB) includes the Journal of Biological Chemistry, Molecular & Cellular Proteomics, and the Journal of Lipid Research. Discover the latest research from ASBMB here.