Compound 800, a natural product isolated from genetically engineered pseudomonas: Proposed structure, reactivity, and putative relation to heme d1

Biochemistry

Volumn 43, Issue 33, 2004, Pages 10730-10738

  Youn, Hyung Sun ^a   Liang, Qiaoli ^a   Cha, Jin K ^a,c   Cai, Mengli ^b   Timkovich, Russell ^a  

^a UNIVERSITY OF ALABAMA   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^c WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; ESCHERICHIA COLI; GENES; NUCLEAR MAGNETIC RESONANCE; X RAY PHOTOELECTRON SPECTROSCOPY;

NATURAL PRODUCTS; PLASMID;

BIOCHEMISTRY;

CHLORINE DERIVATIVE; COMPOUND 800; EPOXIDE; HEME DERIVATIVE; INORGANIC ACID; NATURAL PRODUCT; NITRITE REDUCTASE; PRECORRIN 2; PYRROLE DERIVATIVE; SIROHYDROCHLORIN; SULFOXIDE; TETRAPYRROLE DERIVATIVE; UNCLASSIFIED DRUG; UROPORPHYRINOGEN;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; DENITRIFICATION; ESCHERICHIA COLI; GENE; GENE CLUSTER; GENETIC ENGINEERING; HEATING; IN VITRO STUDY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NIRFDLGH GENE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN SYNTHESIS; PSEUDOMONAS; PSEUDOMONAS STUTZERI; STEADY STATE; STRAIN IDENTIFICATION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; X RAY PHOTOELECTRON SPECTROSCOPY;

ENZYMES; ESCHERICHIA COLI; HEME; MOLECULAR STRUCTURE; MULTIGENE FAMILY; PSEUDOMONAS; TETRAPYRROLES; TRANSDUCTION, GENETIC; UROPORPHYRINS;

ESCHERICHIA COLI; NEGIBACTERIA; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS STUTZERI;

EID: 4143059108     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0491954     Document Type: Article

References (31)

1. Zumft, W. G. (1997) Cell Biology and Molecular Basis of Denitrification. Microbiol. Mol Biol Rev. 61, 533-616.
2. Timkovich, R. (2003) in Porphyrin Handbook, Part II (Kadish, K., Smith, K., Guilard, R., Eds.) pp 123-156, Academic Press, San Diego, CA.
3. 1, J. Biol. Chem. 265, 13498-13500.
4. 1 that Establishes its Absolute Configuration as 2R,7R, J. Chem. Soc., Chem. Commun. 1993, 275-277.
5. 1 (Respiratory Nitrite Reductase) from Pseudomonas stutzeri, Eur. J. Biochem. 232, 737-746.
6. Sofia, H. J. Chen, G., Hetzler, B. G., Reyes-Spindola, J. F., and Miller, N. E. (2001) Radical SAM, a Novel Protein Superfamily Linking Unresolved Steps in Familiar Biosynthetic Pathways with Radical Mechanisms: Functional Characterization Using New Analysis and Information Visualization Methods, Nucleic Acids Res. 29, 1097-1106.
7. Parr, S. R., Barber, D., Greenwood, C., Phillips, B. W., and Melling, J. (1976) A Purification Procedure for the Soluble Cytochrome Oxidase and Some Other Respiratory Proteins from Pseudomonas aeruginosa, Biochem. J. 157, 423-430.
8. LeGall, J., Mazza, G., and Dragoni, N. (1965) Le cytochrome c3 de Desulfovibrio gigas, Biochim. Biophys. Acta 90, 383-387.
9. Ishida, T., Ling, Y., Akutsu, H., Ozawa, K., Kawanishi, S., Seto, A., Inubushi, T., and Sano, S. (1998) A Primitive Pathway of Porphyrin Biosynthesis and Enzymology in Desulfovibrio vulgaris, Proc. Natl. Acad. Sci. U.S.A. 95, 4853-4858.
10. 1-Dependent Nitrite Respiration of Pseudomonas stutzeri Consists of a Cluster of Mono-, Di-, and Tetraheme Proteins, FEBS Lett. 279, 205-209.
11. Miller, G. T., Zhang, B., Hardman, J. K., and Timkovich, R. (2000) Converting a c-Type to a b-Type Cytochrome: Met61 to His 61 Mutant of Pseudomonas Cytochrome c-551, Biochemistry 39, 9010-9017.
12. Bagdasarian, M., Lurz, R., Rueckert, B., Franklin, F. C. H., Bagdasarian, M. M., Frey, J., and Timmis, K. N. (1981) Specific-Purpose Purpose Plasmid Cloning Vectors. II. Broad Host Range, High Copy Number, RSF1010-Derived Vectors, and a Host-Vector System for Gene Cloning in Pseudomonas, Gene 16, 237-247.
13. Bagdasarian, M., and Timmis, K. N. (1982) Host: Vector Systems for Gene Cloning in Pseudomonas, Curr. Top. Microbiol Immunol. 96, 47-67.
14. Schmidhauser, T. J., Ditta, G., and Helinski, D. R. (1988) Broad-Host-Range Plasmid Cloning Vectors for Gram-Negative Bacteria, Biotechnology 10, 287-332.
15. Itoh, Y., Watson, J. M., Haas, D., and Leisinger, T. (1984) Genetic and Molecular Characterization of the Pseudomonas Plasmid pVS1, Plasmid 11, 206-220.
16. Matthews, J. C., Burkhalter, R. S., and Timkovich, R. (1998) Evidence for a Atypical Tetrapyrrole Biosynthetic Pathway in Desulfovibrio: Back Conversion of Sirohydrochlorin into Porphyrins, Bioorg. Chem. 26, 221-231.
17. Youn, H.-S., Burkhalter, R. S., and Timkovich, R. (2002) Identification of Hemes and Related Cyclic Tetrapyrroles by Matrix-Assisted Laser Desorption/Ionization and Liquid Secondary Ion Mass Spectrometry, Rapid Commun. Mass Spectrom. 16, 1-6.
18. Bax, A., and Davis, D. G. (1985) Practical Aspects of Two-Dimensional Transverse NOE Spectroscopy, J. Magn. Reson. 63, 207-213.
19. Pelton, J. G., Torchia, D. A., Meadon, N. D., and Roseman, S. (1993) Tautomeric States of the Active-Site Histidines of Phosphorylated and Unphosphorylated IIIG1c, a Signal-Transducing Protein from Escherichia coli Using Two-Dimensional Hetero-nuclear NMR Techniques, Protein Sci. 2, 543-558.
20. Harris, W. F., Burkhalter, R. S., Lin, W., and Timkovich, R. (1993) Enhancement of Bacterial Porphyrin Biosynthesis by Exogenous Aminolevulinic Acid and Isomer Specificity of the Products, Bioorg. Chem. 21, 209-220.
21. Blanche, F., Debussche, L., Thibaut, D., Crouzet, J., and Cameron, B. (1989) Purification and Characterization of S-Adenosyl-L-Methionine: Uroporphyrinogen III Methyltransferase from Pseudomonas dentrificans, J. Bacteriol. 171, 4222-4231.
22. Wu, J.-Y., Siegel, L. M., and Kredich, N. M. (1991) High Level Expression of E. coli NADPH-Sulfite Reductase: Requirement for a Cloned cysG Plasmid to Overcome Limiting Siroheme Cofactor, J. Bacteriol. 173, 325-333.
23. Silverstein, R. M., Bassler, G. C., and Morril, T. (1974) Spectroscopic Identification of Organic Compounds, 3rd ed., Wiley, New York.
24. Chastain, J., and King, R. C. (1985) Handbook of X-ray Phototelectron Spectroscope, Physical Electronics, Inc., Eden Prairie. MN.
25. 13C NMR Assignments for 3- and 8-Episirohydrochlorin Methyl Esters, Magn. Reson. Chem. 35, 650-652.
26. Timkovich, R., Cork, M. S., Gennis, R. B., and Johnson, P. Y. (1985) Proposed Strucutre of Heme d, a Prosthetic Group of Bacterial Terminal Oxidases, J. Am. Chem. Soc. 107,6069-6075.
27. Chiu, J. T., Loewen, P. C., Switala, J., Gennis, R. B., and Timkovich, R. (1989) Proposed Structure for the Prosthetic Group of the Catalase HPII from E. coli. J. Am. Chem. Soc. 111, 7046-7050.
28. 1, Cell 81, 369-377.
29. 1, Bioorg. Chem. 21, 71-82.
30. 1, Biochim. Biophys. Acta 1116, 24-26.
31. Vicente, M. G. H. (1999) in The Porphyrin Handbook (Kadish, K. M., Smith, K. M., and Guilard, R., Eds.) pp 155, Academic Press, San Diego, CA.