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MetaCyc Enzyme: 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase

Gene: ubiF Accession Numbers: G6365 (MetaCyc), b0662, ECK0654

Synonyms: yleB

Species: Escherichia coli K-12 substr. MG1655

Summary:
2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase catalyzes the third monooxygenase reaction in the ubiquinone biosynthesis pathway. The enzyme has not been characterized biochemically.

A ubiF mutant accumulates 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone (MMQ-8) [Young71a, Kwon00d] and has only a slight growth defect [Wallace77]. MMQ-8 itself can function fairly efficiently (~50%) as an electron carrier in the NADH, D-lactate, and glycerol-3-phosphate dehydrogenase systems, but only poorly for the oxidation of succinate [Wallace77]. ubiF mutants also have reduced capacity for uptake of aminoglycoside antibiotics [Muir81] and are resistant to phleomycin, bleomycin, and heat inactivation [Collis89].

Mutants in genes ubiF, ubiH, ubiX, ubiG, and ubiE from the Keio K-12 mutant collection showed elevated resistance to the broad-spectrum antibiotic D-cycloserine (DCS) when grown in complex media, suggesting that they may be involved in DCS sensitivity [Baisa13].

However, genes ubiF and sucB have been shown to be involved in the survival of small populations of slowly, or non-growing bacteria that are phenotypically resistant to antibiotics (referred to as persisters). Mutants in ubiF and sucB from the E. coli Keio deletion mutant library had higher susceptibility to various antibiotics (ampicillin, norfloxacin, gentamicin, tetracycline and trimethoprim) and several different stress conditions, compared with the parent strain. The potential of these genes as new drug and vaccine targets was noted [Ma10].

Reviews: [Meganathan01, Meganathan01a]

Locations: cytosol

Map Position: [694,324 -> 695,499]

Molecular Weight of Polypeptide: 42.954 kD (from nucleotide sequence)

pI: 6.64 [Kwon00d]

Unification Links: ASAP:ABE-0002265 , DIP:DIP-11069N , EchoBASE:EB3422 , EcoGene:EG13658 , EcoliWiki:b0662 , ModBase:P75728 , OU-Microarray:b0662 , PortEco:ubiF , PR:PRO_000024158 , Pride:P75728 , Protein Model Portal:P75728 , RefSeq:NP_415195 , RegulonDB:G6365 , SMR:P75728 , String:511145.b0662 , UniProt:P75728

Relationship Links: InterPro:IN-FAMILY:IPR002938 , InterPro:IN-FAMILY:IPR003042 , InterPro:IN-FAMILY:IPR010971 , InterPro:IN-FAMILY:IPR018168 , Pfam:IN-FAMILY:PF01494 , Prints:IN-FAMILY:PR00420 , Prosite:IN-FAMILY:PS01304

Gene-Reaction Schematic: ?

GO Terms:

Biological Process: GO:0006744 - ubiquinone biosynthetic process Inferred from experiment Inferred by computational analysis [UniProtGOA12, UniProtGOA11, GOA01, Young71a]
GO:0008152 - metabolic process Inferred by computational analysis [GOA01]
GO:0055114 - oxidation-reduction process Inferred by computational analysis [UniProtGOA11, GOA01]
Molecular Function: GO:0005515 - protein binding Inferred from experiment [Rajagopala14]
GO:0008682 - 2-octoprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase activity Inferred from experiment [Kwon00d]
GO:0004497 - monooxygenase activity Inferred by computational analysis [UniProtGOA11]
GO:0016491 - oxidoreductase activity Inferred by computational analysis [UniProtGOA11, GOA01]
GO:0016705 - oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen Inferred by computational analysis [Kwon00d]
GO:0016709 - oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, NAD(P)H as one donor, and incorporation of one atom of oxygen Inferred by computational analysis [GOA01]
GO:0050660 - flavin adenine dinucleotide binding Inferred by computational analysis [GOA01]
Cellular Component: GO:0005829 - cytosol Inferred by computational analysis [DiazMejia09]

MultiFun Terms: metabolism biosynthesis of building blocks cofactors, small molecule carriers menaquinone, ubiquinone

Credits:
Imported from EcoCyc 16-Sep-2014 by Paley S , SRI International


Enzymatic reaction of: 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase

EC Number: 1.14.-.-

6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + a reduced electron acceptor + oxygen <=> 3-demethylubiquinol-8 + an oxidized electron acceptor + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is physiologically favored in the direction shown.

In Pathways: superpathway of chorismate metabolism , superpathway of ubiquinol-8 biosynthesis (prokaryotic) , ubiquinol-8 biosynthesis (prokaryotic)

Credits:
Imported from EcoCyc 16-Sep-2014 by Paley S , SRI International

History:
6/20/2000 (pkarp) Merged genes G211/ubiF and G6365/b0662
Markus Krummenacker on Tue Oct 14, 1997:
Gene object created from Blattner lab Genbank (v. M52) entry.


References

Baisa13: Baisa G, Stabo NJ, Welch RA (2013). "Characterization of Escherichia coli D-cycloserine transport and resistant mutants." J Bacteriol 195(7);1389-99. PMID: 23316042

Collis89: Collis CM, Grigg GW (1989). "An Escherichia coli mutant resistant to phleomycin, bleomycin, and heat inactivation is defective in ubiquinone synthesis." J Bacteriol 1989;171(9);4792-8. PMID: 2475481

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

GOA01: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

Kwon00d: Kwon O, Kotsakis A, Meganathan R (2000). "Ubiquinone (coenzyme Q) biosynthesis in Escherichia coli: identification of the ubiF gene." FEMS Microbiol Lett 2000;186(2);157-61. PMID: 10802164

Ma10: Ma C, Sim S, Shi W, Du L, Xing D, Zhang Y (2010). "Energy production genes sucB and ubiF are involved in persister survival and tolerance to multiple antibiotics and stresses in Escherichia coli." FEMS Microbiol Lett 303(1);33-40. PMID: 20041955

Meganathan01: Meganathan R (2001). "Ubiquinone biosynthesis in microorganisms." FEMS Microbiol Lett 203(2);131-9. PMID: 11583838

Meganathan01a: Meganathan R (2001). "Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms." Vitam Horm 61;173-218. PMID: 11153266

Muir81: Muir ME, Hanwell DR, Wallace BJ (1981). "Characterization of a respiratory mutant of Escherichia coli with reduced uptake of aminoglycoside antibiotics." Biochim Biophys Acta 638(2);234-41. PMID: 7032590

Rajagopala14: Rajagopala SV, Sikorski P, Kumar A, Mosca R, Vlasblom J, Arnold R, Franca-Koh J, Pakala SB, Phanse S, Ceol A, Hauser R, Siszler G, Wuchty S, Emili A, Babu M, Aloy P, Pieper R, Uetz P (2014). "The binary protein-protein interaction landscape of Escherichia coli." Nat Biotechnol 32(3);285-90. PMID: 24561554

UniProtGOA11: UniProt-GOA (2011). "Gene Ontology annotation based on manual assignment of UniProtKB keywords in UniProtKB/Swiss-Prot entries."

UniProtGOA12: UniProt-GOA (2012). "Gene Ontology annotation based on UniPathway vocabulary mapping."

Wallace77: Wallace BJ, Young IG (1977). "Aerobic respiration in mutants of Escherichia coli accumulating quinone analogues of ubiquinone." Biochim Biophys Acta 461(1);75-83. PMID: 195601

Young71a: Young IG, McCann LM, Stroobant P, Gibson F (1971). "Characterization and genetic analysis of mutant strains of Escherichia coli K-12 accumulating the biquinone precursors 2-octaprenyl-6-methoxy-1,4-benzoquinone and 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone." J Bacteriol 1971;105(3);769-78. PMID: 4323297


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Thu Nov 27, 2014, BIOCYC14B.