The Enzyme Database

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EC 1.3.99.38     
Accepted name: menaquinone-9 β-reductase
Reaction: menaquinone-9 + reduced acceptor = β-dihydromenaquinone-9 + acceptor
For diagram of vitamin K biosynthesis, click here
Glossary: β-dihydromenaquinone-9 = MK-9(II-H2) = 2-methyl-3-[(2E,10E,14E,18E,22E,26E,30E,33E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,10,14,18,22,26,30,33-octaen-1-yl]naphthalene-1,4-dione
Other name(s): MenJ
Systematic name: menaquinone-9 oxidoreductase (β-dihydromenaquinone-9-forming)
Comments: The enzyme from the bacterium Mycobacterium tuberculosis reduces the β-isoprene unit of menaquinone-9, forming the predominant form of menaquinone found in mycobacteria. Contains FAD.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Upadhyay, A., Fontes, F.L., Gonzalez-Juarrero, M., McNeil, M.R., Crans, D.C., Jackson, M. and Crick, D.C. Partial saturation of menaquinone in Mycobacterium tuberculosis: function and essentiality of a novel reductase, MenJ. ACS Cent. Sci. 1 (2015) 292–302. [DOI] [PMID: 26436137]
[EC 1.3.99.38 created 2017]
 
 
EC 1.14.15.27     
Accepted name: β-dihydromenaquinone-9 ω-hydroxylase
Reaction: β-dihydromenaquinone-9 + 2 reduced ferredoxin [iron-sulfur] cluster + O2 = ω-hydroxy-β-dihydromenaquinone-9 + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
For diagram of vitamin K biosynthesis, click here
Glossary: β-dihydromenaquinone-9 = MK-9(II-H2) = 2-methyl-3-[(2E,10E,14E,18E,22E,26E,30E,33E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,10,14,18,22,26,30,33-octaen-1-yl]naphthalene-1,4-dione
Other name(s): cyp128 (gene name)
Systematic name: β-dihydromenaquinone-9,reduced ferredoxin:oxygen oxidoreductase (ω-hydroxylating)
Comments: The bacterial cytochrome P-450 enzyme is involved in the biosynthesis of ω-sulfo-β-dihydromenaquinone-9 by members of the Mycobacterium tuberculosis complex.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Holsclaw, C.M., Sogi, K.M., Gilmore, S.A., Schelle, M.W., Leavell, M.D., Bertozzi, C.R. and Leary, J.A. Structural characterization of a novel sulfated menaquinone produced by stf3 from Mycobacterium tuberculosis. ACS Chem. Biol. 3 (2008) 619–624. [PMID: 18928249]
2.  Sogi, K.M., Holsclaw, C.M., Fragiadakis, G.K., Nomura, D.K., Leary, J.A. and Bertozzi, C.R. Biosynthesis and regulation of sulfomenaquinone, a metabolite associated with virulence in Mycobacterium tuberculosis. ACS Infect Dis 2 (2016) 800–806. [PMID: 27933784]
[EC 1.14.15.27 created 2018]
 
 
EC 2.8.2.40     
Accepted name: ω-hydroxy-β-dihydromenaquinone-9 sulfotransferase
Reaction: 3′-phosphoadenylyl sulfate + ω-hydroxy-β-dihydromenaquinone-9 = adenosine 3′,5′-bisphosphate + ω-sulfo-β-dihydromenaquinone-9
Glossary: β-dihydromenaquinone-9 = MK-9(II-H2) = 2-methyl-3-[(2E,10E,14E,18E,22E,26E,30E,33E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,10,14,18,22,26,30,33-octaen-1-yl]naphthalene-1,4-dione
Other name(s): stf3 (gene name)
Systematic name: 3′-phosphoadenylyl-sulfate:ω-hydroxy-β-dihydromenaquinone-9 sulfotransferase
Comments: The enzyme catalyses the last step in the production of ω-sulfo-β-dihydromenaquinone-9 by members of the Mycobacterium tuberculosis complex.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Mougous, J.D., Senaratne, R.H., Petzold, C.J., Jain, M., Lee, D.H., Schelle, M.W., Leavell, M.D., Cox, J.S., Leary, J.A., Riley, L.W. and Bertozzi, C.R. A sulfated metabolite produced by stf3 negatively regulates the virulence of Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. USA 103 (2006) 4258–4263. [PMID: 16537518]
2.  Holsclaw, C.M., Sogi, K.M., Gilmore, S.A., Schelle, M.W., Leavell, M.D., Bertozzi, C.R. and Leary, J.A. Structural characterization of a novel sulfated menaquinone produced by stf3 from Mycobacterium tuberculosis. ACS Chem. Biol. 3 (2008) 619–624. [PMID: 18928249]
[EC 2.8.2.40 created 2021]
 
 


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