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EC Tree
IUBMB Comments Vitamin K 2,3-epoxide is reduced to 3-hydroxy- (and 2-hydroxy-) vitamin K by 1,4-dithiothreitol, which is oxidized to a disulfide. Not inhibited by warfarin [cf. EC 1.17.4.4, vitamin-K-epoxide reductase (warfarin-sensitive)].
The enzyme appears in viruses and cellular organisms
Synonyms
vkorl1, vitamin ko reductase, vitamin k 2,3 epoxide reductase, non-vkor, vkor-like1,
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EC 1.1.4.2
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formerly
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reductase, vitamin K epoxide (warfarin-insensitive)
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vitamin K 2,3 epoxide reductase
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vitamin K epoxide reductase
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vitamin K epoxide reductase (warfarin-insensitive)
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vitamin K epoxide reductase-like1
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vitamin KO reductase
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3-hydroxy-2-methyl-3-phytyl-2,3-dihydro-1,4-naphthoquinone + oxidized dithiothreitol = 2,3-epoxy-2-methyl-3-phytyl-2,3-dihydro-1,4-naphthoquinone + 1,4-dithiothreitol
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3-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone:oxidized-dithiothreitol oxidoreductase
Vitamin K 2,3-epoxide is reduced to 3-hydroxy- (and 2-hydroxy-) vitamin K by 1,4-dithiothreitol, which is oxidized to a disulfide. Not inhibited by warfarin [cf. EC 1.17.4.4, vitamin-K-epoxide reductase (warfarin-sensitive)].
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2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
2-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone + oxidized dithiothreitol
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2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
3-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone + oxidized dithiothreitol
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i.e. vitamin K 2,3-epoxide
i.e. 3-hydroxy-2,3-dihydro-vitamin K
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
additional information
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
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additional information
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the enzyme, driven by the reducing agent DTT, reduces both vitamin K 2,3-epoxide and vitamin K to the activated hydroquinone form
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additional information
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the enzyme, driven by the reducing agent DTT, reduces both vitamin K 2,3-epoxide and vitamin K to the activated hydroquinone form
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2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
2-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone + oxidized dithiothreitol
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
additional information
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
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additional information
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the enzyme, driven by the reducing agent DTT, reduces both vitamin K 2,3-epoxide and vitamin K to the activated hydroquinone form
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additional information
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the enzyme, driven by the reducing agent DTT, reduces both vitamin K 2,3-epoxide and vitamin K to the activated hydroquinone form
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additional information
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2-mercaptoethanol, reduced GSH, 1,2-ethanediol, or reduced lipoic acid are ineffective as cofactors
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glycerol
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concentrations up to 30% v/v inhibit enzyme activity up to 88%
additional information
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not inhibited by warfarin
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additional information
non-VKOR, warfarin-sensitive enzyme, while hVKORL is mainly insensitive to inhibition by warfarin, but about 30% of hVKORL1 is inhibited by 0.005 mM warfarin, VKORL1 is warfarin sensitive, but not affect warfarin dosage requirements
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additional information
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non-VKOR, warfarin-sensitive enzyme, while hVKORL is mainly insensitive to inhibition by warfarin, but about 30% of hVKORL1 is inhibited by 0.005 mM warfarin, VKORL1 is warfarin sensitive, but not affect warfarin dosage requirements
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additional information
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evaluation of warfarin resistance using TALENs-mediated vitamin K epoxide reductase knockout HEK293 cells, overview
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additional information
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VKORC1 mutant Y137F is resistant against inhibition by warfarin, but not against inhibition by other antocoagulants, overview
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3-[(3-cholamidopropyl)-dimethyl-ammonio]1-propane sulfonate
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CHAPS, activation
dithiothreitol
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non-physiological cofactor
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Neoplasms
Structural and functional insights into human vitamin K epoxide reductase and vitamin K epoxide reductase-like1.
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0.00007
brodifacoum
Rattus norvegicus
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mutant Y137F, pH 7.4, 37°C
0.00061
bromadiolone
Rattus norvegicus
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mutant Y137F, pH 7.4, 37°C
0.0016
chlorophacinone
Rattus norvegicus
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mutant Y137F, pH 7.4, 37°C
0.0001
Difenacoum
Rattus norvegicus
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mutant Y137F, pH 7.4, 37°C
0.00005
difethialone
Rattus norvegicus
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mutant Y137F, pH 7.4, 37°C
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brenda
gene Vkorc1, VKORC1 mutant Y137F
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UniProt
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integral membrane protein
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evolution
VKORL1, EC 1.1.4.2, is more highly conserved among vertebrates than its evolutionary relative VKOR, EC 1.1.4.1. The human paralogous proteins are 42-60% identical
metabolism
vitamin K cycle, overview
physiological function
vitamin K dependent oxidative protection is independent of VKOR inhibition by warfarin and GGCX inhibition by 2-chloro-vitamin K1, which indicates that vitamin K plays potential physiological roles outside of the realm of carboxylation. The hVKORL1 turnover rate for vitamin K 2,3-epoxide reductase activity is significantly slower than for hVKOR, EC 1.1.4.1. the physiological role for VKORL1 reduction of vitamin K 2,3-epoxide is minimal
additional information
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conserved loop cysteines in VKOR are not required for active site regeneration after each cycle of oxidation. Missense mutations identified in the VKOR coding region, especially hotspot mutation at position 139, lead to a VKOR molecule more resistant to warfarin inhibition, thus requiring higher therapeutic warfarin doses
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VKORL_HUMAN
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19836
Swiss-Prot
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VKOR_SYNJB
Synechococcus sp. (strain JA-2-3B'a(2-13))
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0
30593
Swiss-Prot
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12400
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2 * 12400, SDS-PAGE
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dimer
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2 * 12400, SDS-PAGE
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L128R
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the naturally occuring mutant shows significantly increased warfarin resistance, but its enzyme activity is 2fold higher compared to wild-type VKOR
W59L
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the naturally occuring mutant shows significantly increased warfarin resistance, but its enzyme activity is 2fold higher compared to wild-type VKOR
W59R
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the naturally occuring mutant shows significantly increased warfarin resistance, but its enzyme activity is similar to wild-type VKOR
additional information
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knockout of endogenous VKOR activity, i.e. VKOR and VKORC1L1 enzymes, in HEK-293 cells by transcription activator-like effector nucleases (TALENs)-mediated genome editing, overview
additional information
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the W59R mutant has lower activity but higher warfarin resistance than the W59L mutant, warfarin resistance evaluation of the naturally occurring VKOR mutants, overview
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high ionic strength inactivates during purification
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-70°C, microsomal preparation, stable for months
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expression of thec-myc-tagged enzyme mutant Y137F in Pichia pastoris membranes
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the VKOR-like gene that encodes hVKORL1 that is found on chromosome 7, sequence comparisons
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Mukharji, I.; Silverman, R.B.
Purification of a vitamin K epoxide reductase that catalyzes conversion of vitamin K 2,3-epoxide to 3-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone
Proc. Natl. Acad. Sci. USA
82
2713-2717
1985
Bos taurus
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Hodroge, A.; Longin-Sauvageon, C.; Fourel, I.; Benoit, E.; Lattard, V.
Biochemical characterization of spontaneous mutants of rat VKORC1 involved in the resistance to antivitamin K anticoagulants
Arch. Biochem. Biophys.
515
14-20
2011
Rattus norvegicus
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Van Horn, W.D.
Structural and functional insights into human vitamin K epoxide reductase and vitamin K epoxide reductase-like1
Crit. Rev. Biochem. Mol. Biol.
48
357-372
2013
Homo sapiens (Q8N0U8), Homo sapiens
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Tie, J.K.; Jin, D.Y.; Tie, K.; Stafford, D.W.
Evaluation of warfarin resistance using TALENs-mediated vitamin K epoxide reductase knockout HEK293 cells
J. Thromb. Haemost.
11
1556-1564
2013
Homo sapiens
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