Note to users. If you're seeing this message, it means that your browser cannot find this page's style/presentation instructions -- or possibly that you are using a browser that does not support current Web standards. Find out more about why this message is appearing, and what you can do to make your experience of our site the best it can be.

Site Tools

  • AAAS
  • Subscribe
  • Feedback

Site Search

Search Advanced

Science 25 May 1990:
Vol. 248. no. 4958, pp. 981 - 987
DOI: 10.1126/science.2111581
Prev | Table of Contents | Next

Articles

Science, Vol 248, Issue 4958, 981-987
Copyright © 1990 by American Association for the Advancement of Science

articles

A new redox cofactor in eukaryotic enzymes: 6-hydroxydopa at the active site of bovine serum amine oxidase

SM Janes, D Mu, D Wemmer, AJ Smith, S Kaur, D Maltby, AL Burlingame, and JP Klinman

Department of Chemistry, University of California, Berkeley 94720.

An active site, cofactor-containing peptide has been obtained in high yield from bovine serum amine oxidase. Sequencing of this pentapeptide indicates: Leu-Asn-X-Asp-Tyr. Analysis of the peptide by mass spectrometry, ultraviolet-visible spectroscopy, and proton nuclear magnetic resonance leads to the identification of X as 6-hydroxydopa. This result indicates that, contrary to previous proposals, pyrroloquinoline quinone is not the active site cofactor in mammalian copper amine oxidases. Although 6-hydroxydopa has been implicated in neurotoxicity, the data presented suggest that this compound has a functional role at an enzyme active site.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Copper Distributed by Atx1 Is Available to Copper Amine Oxidase 1 in Schizosaccharomyces pombe.
C. Peter, J. Laliberte, J. Beaudoin, and S. Labbe (2008)
Eukaryot. Cell 7, 1781-1794
   Abstract »    Full Text »    PDF »
Purification and Characterization of a Copper-Containing Amine Oxidase from Mycobacterium Sp. Strain JC1 DSM 3803 Grown on Benzylamine.
H.-I. Lee, Y. M. Kim, and Y. T. Ro (2008)
J. Biochem. 144, 107-114
   Abstract »    Full Text »    PDF »
Multiple Binding Sites for Substrates and Modulators of Semicarbazide-Sensitive Amine Oxidases: Kinetic Consequences.
A. Holt, D. J. Smith, L. Cendron, G. Zanotti, A. Rigo, and M. L. Di Paolo (2008)
Mol. Pharmacol. 73, 525-538
   Abstract »    Full Text »    PDF »
An Activated Glutamate Residue Identified in Photosystem II at the Interface between the Manganese-stabilizing Subunit and the D2 Polypeptide.
S. Rexroth, C. C. L. Wong, J. H. Park, J. R. Yates III, and B. A. Barry (2007)
J. Biol. Chem. 282, 27802-27809
   Abstract »    Full Text »    PDF »
Exploring Molecular Oxygen Pathways in Hansenula polymorpha Copper-containing Amine Oxidase.
B. J. Johnson, J. Cohen, R. W. Welford, A. R. Pearson, K. Schulten, J. P. Klinman, and C. M. Wilmot (2007)
J. Biol. Chem. 282, 17767-17776
   Abstract »    Full Text »    PDF »
Involvement of a Putative [Fe-S]-cluster-binding Protein in the Biogenesis of Quinohemoprotein Amine Dehydrogenase.
K. Ono, T. Okajima, M. Tani, S. Kuroda, D. Sun, V. L. Davidson, and K. Tanizawa (2006)
J. Biol. Chem. 281, 13672-13684
   Abstract »    Full Text »    PDF »
Mechanisms of ammonia activation and ammonium ion inhibition of quinoprotein methanol dehydrogenase: A computational approach.
S. Y. Reddy and T. C. Bruice (2004)
PNAS 101, 15887-15892
   Abstract »    Full Text »    PDF »
Molecular Cloning of Complementary DNA Encoding Mouse Seminal Vesicle-Secreted Protein SVS I and Demonstration of Homology with Copper Amine Oxidases.
A. Lundwall, J. Malm, A. Clauss, C. Valtonen-Andre, and A. Y. Olsson (2003)
Biol Reprod 69, 1923-1930
   Abstract »    Full Text »    PDF »
Novel Glyoxysomal Protein Kinase, GPK1, Identified by Proteomic Analysis of Glyoxysomes in Etiolated Cotyledons of Arabidopsis thaliana.
Y. Fukao, M. Hayashi, I. Hara-Nishimura, and M. Nishimura (2003)
Plant Cell Physiol. 44, 1002-1012
   Abstract »    Full Text »    PDF »
In Vitro Metabolism of Tresperimus by Human Vascular Semicarbazide-Sensitive Amine Oxidase.
P. Claud, Y. Artur, and R. Laine (2002)
Drug Metab. Dispos. 30, 747-755
   Abstract »    Full Text »    PDF »
Crystal Structure of Quinohemoprotein Alcohol Dehydrogenase from Comamonas testosteroni. STRUCTURAL BASIS FOR SUBSTRATE OXIDATION AND ELECTRON TRANSFER.
A. Oubrie, H. J. Rozeboom, K. H. Kalk, E. G. Huizinga, and B. W. Dijkstra (2002)
J. Biol. Chem. 277, 3727-3732
   Abstract »    Full Text »    PDF »
How many ways to craft a cofactor?.
J. P. Klinman (2001)
PNAS 98, 14766-14768
   Full Text »    PDF »
The Covalent Structure of the Small Subunit from Pseudomonas putida Amine Dehydrogenase Reveals the Presence of Three Novel Types of Internal Cross-linkages, All Involving Cysteine in a Thioether Bond.
I. Vandenberghe, J.-K. Kim, B. Devreese, A. Hacisalihoglu, H. Iwabuki, T. Okajima, S.'i. Kuroda, O. Adachi, J. A. Jongejan, J. A. Duine, et al. (2001)
J. Biol. Chem. 276, 42923-42931
   Abstract »    Full Text »    PDF »
Homemade cofactors: Self-processing in galactose oxidase.
L. Xie and W. A. van der Donk (2001)
PNAS 98, 12863-12865
   Full Text »    PDF »
From the Cover: Crystal structure of the precursor of galactose oxidase: An unusual self-processing enzyme.
S. J. Firbank, M. S. Rogers, C. M. Wilmot, D. M. Dooley, M. A. Halcrow, P. F. Knowles, M. J. McPherson, and S. E. V. Phillips (2001)
PNAS 98, 12932-12937
   Abstract »    Full Text »    PDF »
Involvement of Semicarbazide-Sensitive Amine Oxidase in Tresperimus Metabolism in Human and in Rat.
P. Claud, P. Padovani, J.-P. Guichard, Y. Artur, and R. Lainé (2001)
Drug Metab. Dispos. 29, 735-741
   Abstract »    Full Text »
Plasma semicarbazide-sensitive amine oxidase (SSAO) is an independent prognostic marker for mortality in chronic heart failure.
F Boomsma, P.J de Kam, G Tjeerdsma, A.H van Den Meiracker, and D.J van Veldhuisen (2000)
Eur. Heart J. 21, 1859-1863
   Abstract »    PDF »
Probing the Structure of Photosystem II with Amines and Phenylhydrazine.
L. B. Anderson, A. J. A. Ouellette, and B. A. Barry (2000)
J. Biol. Chem. 275, 4920-4927
   Abstract »    Full Text »    PDF »
Active-site structure of the soluble quinoprotein glucose dehydrogenase complexed with methylhydrazine: A covalent cofactor-inhibitor complex.
A. Oubrie, H. J. Rozeboom, and B. W. Dijkstra (1999)
PNAS 96, 11787-11791
   Abstract »    Full Text »    PDF »
Molecular Cloning of a Major mRNA Species in Murine 3T3 Adipocyte Lineage. DIFFERENTIATION-DEPENDENT EXPRESSION, REGULATION, AND IDENTIFICATION AS SEMICARBAZIDE-SENSITIVE AMINE OXIDASE.
M. Moldes, B. Feve, and J. Pairault (1999)
J. Biol. Chem. 274, 9515-9523
   Abstract »    Full Text »    PDF »
Probing the "Active Site" of Diamine Oxidase: Structure-Activity Relations for Histamine Potentiation by O-Alkylhydroxylamines on Colonic Epithelium.
A. High, T. Prior, R. A. Bell, and P. K. Rangachari (1999)
J. Pharmacol. Exp. Ther. 288, 490-501
   Abstract »    Full Text »
Isolation, Structural Characterization, and Chromosomal Mapping of the Mouse Vascular Adhesion Protein-1 Gene and Promoter.
P. Bono, M. Salmi, D. J. Smith, I. Leppanen, N. Horelli-Kuitunen, A. Palotie, and S. Jalkanen (1998)
J. Immunol. 161, 2953-2960
   Abstract »    Full Text »    PDF »
Characterization of Euphorbia characias Latex Amine Oxidase.
A. Padiglia, R. Medda, A. Lorrai, B. Murgia, J. Z. Pedersen, A. Finazzi Agró, and G. Floris (1998)
Plant Physiology 117, 1363-1371
   Abstract »    Full Text »
Cloning and Characterization of Mouse Vascular Adhesion Protein-1 Reveals a Novel Molecule with Enzymatic Activity.
P. Bono, M. Salmi, D. J. Smith, and S. Jalkanen (1998)
J. Immunol. 160, 5563-5571
   Abstract »    Full Text »    PDF »
Amine binding and oxidation at the catalytic site for photosynthetic water oxidation.
A. J. A. Ouellette, L. B. Anderson, and B. A. Barry (1998)
PNAS 95, 2204-2209
   Abstract »    Full Text »    PDF »
Effect of Metal on 2,4,5-Trihydroxyphenylalanine (Topa) Quinone Biogenesis in the Hansenula polymorpha Copper Amine Oxidase.
D. Cai, N. K. Williams, and J. P. Klinman (1997)
J. Biol. Chem. 272, 19277-19281
   Abstract »    Full Text »    PDF »
Purification and Characterization of a Membrane-bound Deglycating Enzyme (1-Deoxyfructosyl Alkyl Amino Acid Oxidase, EC 1.5.3) from a Pseudomonas sp. Soil Strain.
A. K. Saxena, P. Saxena, and V. M. Monnier (1996)
J. Biol. Chem. 271, 32803-32809
   Abstract »    Full Text »    PDF »
New Quinocofactors in Eukaryotes.
J. P. Klinman and J. P. Klinman (1996)
J. Biol. Chem. 271, 27189-27192
   Full Text »    PDF »
Role of Conserved Asn-Tyr-Asp-Tyr Sequence in Bacterial Copper/2,4,5-Trihydroxyphenylalanyl Quinone-containing Histamine Oxidase.
Y.-H. Choi, R. Matsuzaki, S. Suzuki, and K. Tanizawa (1996)
J. Biol. Chem. 271, 22598-22603
   Abstract »    Full Text »    PDF »
Biosynthesis of Topa Quinone Cofactor in Bacterial Amine Oxidases.
N. Nakamura, R. Matsuzaki, Y.-H. Choi, K. Tanizawa, and J. Sanders-Loehr (1996)
J. Biol. Chem. 271, 4718-4724
   Abstract »    Full Text »    PDF »
Cloning and Molecular Analysis of the Pea Seedling Copper Amine Oxidase.
A. J. Tipping and M. J. McPherson (1995)
J. Biol. Chem. 270, 16939-16946
   Abstract »    Full Text »    PDF »
Copper/Topa Quinone-containing Histamine Oxidase from Arthrobacter globiformis.
Y.-H. Choi, R. Matsuzaki, T. Fukui, E. Shimizu, T. Yorifuji, H. Sato, Y. Ozaki, and K. Tanizawa (1995)
J. Biol. Chem. 270, 4712-4720
   Abstract »    Full Text »    PDF »
Tandem Mass Spectrometry and Structural Elucidation of Glycopeptides from a Hydroxyproline-rich Plant Cell Wall Glycoprotein Indicate That Contiguous Hydroxyproline Residues Are the Major Sites of Hydroxyproline O-Arabinosylation.
M. J. Kieliszewski, M. O'Neill, J. Leykam, and R. Orlando (1995)
J. Biol. Chem. 270, 2541-2549
   Abstract »    Full Text »    PDF »
A new cofactor in a prokaryotic enzyme: tryptophan tryptophylquinone as the redox prosthetic group in methylamine dehydrogenase.
W. McIntire, D. Wemmer, A Chistoserdov, and M. Lidstrom (1991)
Science 252, 817-824
   Abstract »    PDF »
Crystal Structure of Quinohemoprotein Amine Dehydrogenase from Pseudomonas putida. IDENTIFICATION OF A NOVEL QUINONE COFACTOR ENCAGED BY MULTIPLE THIOETHER CROSS-BRIDGES.
A. Satoh, J.-K. Kim, I. Miyahara, B. Devreese, I. Vandenberghe, A. Hacisalihoglu, T. Okajima, S.'i. Kuroda, O. Adachi, J. A. Duine, et al. (2002)
J. Biol. Chem. 277, 2830-2834
   Abstract »    Full Text »    PDF »
Structure of a quinohemoprotein amine dehydrogenase with an uncommon redox cofactor and highly unusual crosslinking.
S. Datta, Y. Mori, K. Takagi, K. Kawaguchi, Z.-W. Chen, T. Okajima, S.'i. Kuroda, T. Ikeda, K. Kano, K. Tanizawa, et al. (2001)
PNAS 98, 14268-14273
   Abstract »    Full Text »    PDF »


To Advertise     Find Products

Science. ISSN 0036-8075 (print), 1095-9203 (online)