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EC Tree
The enzyme appears in viruses and cellular organisms
Synonyms
2,6-dihydroxypyridine hydroxylase, 2,6-dihydroxypyridine oxidase, 2,6-dihydroxypyridine-3-hydroxylase,
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2,6-dihydroxypyridine hydroxylase
2,6-dihydroxypyridine oxidase
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2,6-dihydroxypyridine-3-hydroxylase
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2,6-dihydroxypyridine hydroxylase
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2,6-dihydroxypyridine hydroxylase
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2,6-dihydroxypyridine hydroxylase
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2,6-dihydroxypyridine + NADH + H+ + O2 = 2,3,6-trihydroxypyridine + NAD+ + H2O
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2,6-dihydroxypyridine,NADH:oxygen oxidoreductase (3-hydroxylating)
A flavoprotein.
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2,6-dihydroxypyridine + NADH + electron acceptor
2,3,6-trihydroxypyridine + NAD+ + reduced electron acceptor
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methylene blue and 2,6-dichlorophenol-indophenol can act as alternative electron acceptors
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2,6-dihydroxypyridine + NADH + O2
2,3,6-trihydroxypyridine + NAD+ + H2O
additional information
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2-hydroxypyridine, 3-hydroxypyridine, 4-hydroxypyridine, 2,5-dihydroxypyridine, 2,6-dipicolinic acid, p-hydroxybenzoic acid, nicotinic acid and nicotine are no substrates for this enzyme
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2,6-dihydroxypyridine + NADH + O2
2,3,6-trihydroxypyridine + NAD+ + H2O
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2,6-dihydroxypyridine + NADH + O2
2,3,6-trihydroxypyridine + NAD+ + H2O
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2,6-dihydroxypyridine + NADH + O2
2,3,6-trihydroxypyridine + NAD+ + H2O
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pyridine ring cleavage follows in a second reaction
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2,6-dihydroxypyridine + NADH + O2
2,3,6-trihydroxypyridine + NAD+ + H2O
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product dimerizes spontaneously in the presence of oxygen to form a blue pigment
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2,6-dihydroxypyridine + NADH + O2
2,3,6-trihydroxypyridine + NAD+ + H2O
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NADPH
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less effective than NADH
FAD
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FAD
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2 mol FAD per dimer
NADH
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NADH
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no reaction with NADPH
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2,6-dihydroxynicotinamide
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55% inhibition at 0.1 mM, reversible inhibitor
2-Hydroxypyridine
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48% inhibition at 0.1 mM, reversible inhibitor
Cu2+
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50% inhibition at 0.017 mM
Hg2+
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50% inhibition at 0.005 mM
NaN3
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50% inhibition at 2 mM
p-chloromercuribenzoate
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50% inhibition at 0.01 mM
resorcine
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51% inhibition at 0.1 mM, reversible inhibitor
Zn2+
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50% inhibition at 0.7 mM
2,3-dihydroxypyridine
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100% inhibition at 0.1 mM, irreversible inhibitor
2,6-dimethoxypyridine
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100% inhibition at 0.1 mM, irreversible inhibitor
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EDTA
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38% activation at 0.05 mM
KCN
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18% activation at 0.5 mM
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0.0083
2,6-Dihydroxypyridine
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pH 8, 20°C
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SwissProt
brenda
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SwissProt
brenda
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SwissProt
brenda
formerly Arthrobacter oxidans
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brenda
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brenda
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DHPH_PAENI
397
0
43400
Swiss-Prot
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A0A344UWV0_9ACTN
363
1
39142
TrEMBL
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A0A1U7CNA8_9BACT
383
0
42213
TrEMBL
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A0A1V2MW38_9ACTN
398
0
41799
TrEMBL
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A0A2S6QFU3_9PROT
437
1
49371
TrEMBL
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A0A5E6U7I4_PSEFL
378
0
41371
TrEMBL
-
A0A5S9R8U8_MYCVN
387
0
42104
TrEMBL
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A0A2H5YR67_9BACT
421
0
46221
TrEMBL
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A0A2S6TBY0_9PROT
245
0
27219
TrEMBL
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A0A2S6TX15_9PROT
199
0
22313
TrEMBL
-
A0A6G8NR49_9BURK
411
0
44507
TrEMBL
-
A0A6G8NPS7_9BURK
382
0
41404
TrEMBL
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A0A2Z4AD65_9BACT
419
0
46655
TrEMBL
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A0A6S7BQ45_9BURK
382
1
41780
TrEMBL
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A0A6S7F129_9BURK
396
0
43781
TrEMBL
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A0A6S7EVK6_9BURK
403
0
44525
TrEMBL
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A0A2S6T785_9PROT
194
0
22047
TrEMBL
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A0A3Q9J0N4_9MICO
377
0
40312
TrEMBL
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A0A653URX9_9MICC
397
0
43715
TrEMBL
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A0A7G9MU29_9BURK
217
0
23293
TrEMBL
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A0A2W1K0K8_9CYAN
391
1
43563
TrEMBL
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A0A5M9IS06_9PSED
380
0
41529
TrEMBL
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A0A5E7AW33_PSEFL
406
0
44324
TrEMBL
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A0A387HAA1_9ACTN
369
0
40319
TrEMBL
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A0A6G8NPV5_9BURK
376
0
40306
TrEMBL
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A0A2S6QI92_9PROT
422
0
47861
TrEMBL
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A0A653RIQ8_9MICC
397
0
43248
TrEMBL
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A0A5S9NSE8_9RHIZ
371
0
40235
TrEMBL
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A1SE94_NOCSJ
Nocardioides sp. (strain ATCC BAA-499 / JS614)
394
0
42131
TrEMBL
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43400
2 * 43400, crystal structure
89000
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sucrose density gradient centrifugation
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homodimer
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homodimer
2 * 43400, crystal structure
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C323S
mutation did not cause any relevant structural disturbance
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7
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most stable in 50 mM potassium phosphate buffer
439040
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15
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30% loss of activity in 10 min
30
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complete loss of activity in 10 min
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dialysis against 1.5 M guanidinium hydrochloride removes FAD, no renaturation possible
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Acetone
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complete loss of activity
Ethanol
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stabilizes during preparative manipulations
Glycerol
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stabilizes during preparative manipulations
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expressed in Escherichia coli XL-1 blue
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His-tag, expressed in Escherichia coli
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after removal of FAD through precipitation with 50% (NH4)2SO4 at pH 2.0, incubation with 0.1 mM FAD leeds to 90% activity recovery
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Baitsch, D.; Sandu, C.; Brandsch, R.; Igloi, G.L.
Gene cluster on pAO1 of Arthrobacter nicotinovorans involved in degradation of the plant alkaloid nicotine: cloning, purification, and characterization of 2,6-dihydroxypyridine 3-hydroxylase
J. Bacteriol.
183
5262-5267
2001
Paenarthrobacter nicotinovorans
brenda
Holmes, P.E.; Rittenberg, S.C.
The bacterial oxidation of nicotine. VII. Partial purification and properties of 2,6-dihydroxypyridine oxidase
J. Biol. Chem.
247
7622-7627
1972
Paenarthrobacter nicotinovorans
brenda
Holmes, P.E.; Rittenberg, S.C.; Knackmuss, H.J.
The bacterial oxidation of nicotine. 8. Synthesis of 2,3,6-trihydroxypyridine and accumulation and partial characterization of the product of 2,6-dihydroxypyridine oxidation
J. Biol. Chem.
247
7628-7633
1972
Paenarthrobacter nicotinovorans
brenda
Ganas, P.; Sachelaru, P.; Mihasan, M.; Igloi, G.L.; Brandsch, R.
Two closely related pathways of nicotine catabolism in Arthrobacter nicotinovorans and Nocardioides sp. strain JS614
Arch. Microbiol.
189
511-517
2008
Nocardioides sp. (A1SE94), Paenarthrobacter nicotinovorans (Q93NG3), Paenarthrobacter nicotinovorans, Nocardioides sp. JS614 / ATCC BAA-499 (A1SE94)
brenda
Treiber, N.; Schulz, G.
Structure of 2,6-dihydroxypyridine 3-hydroxylase from a nicotine-degrading pathway
J. Mol. Biol.
379
94-104
2008
Paenarthrobacter nicotinovorans (Q93NG3), Paenarthrobacter nicotinovorans
brenda
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1.14.13.10 2,6-dihydroxypyridine 3-monooxygenase
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