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Information on EC 1.14.13.73 - tabersonine 16-hydroxylase Word Map on EC 1.14.13.73
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The expected taxonomic range for this enzyme is: Catharanthus roseus
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tabersonine 16-hydroxylase
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tabersonine + NADPH + H+ + O2 = 16-hydroxytabersonine + NADP+ + H2O
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Indole alkaloid biosynthesis
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vindoline and vinblastine biosynthesis
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tabersonine,NADPH:oxygen oxidoreductase (16-hydroxylating)
A heme-thiolate protein (P-450).
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oxygenase, tabersonine 16-mono-
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tabersonine 16-monooxygenase
CYP71D12
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T16H
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tabersonine 16-monooxygenase
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tabersonine 16-monooxygenase
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UniProt
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50 different flowering cultivars, one low vindoline accumulating cultivar Little Delicata
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CYP71D12; cultivar Pacifica Pink
UniProt
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line CP3a
Uniprot
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metabolism
the enzyme catalyzes the first step in the biosynthesis of vindoline, which constitutes the main terpenoid indole alkaloid accumulated in leaves of Catharanthus roseus, spatial organization of the vindoline biosynthetic pathway, overview. Absence of metabolic channeling in the vindoline biosynthetic pathway. Importance of inter- and intracellular translocations of intermediates during the vindoline biosynthesis and potential regulatory role, overview
metabolism
CYP71D12 (isoform T16H2) plays a role in the biosynthesis of vindoline in flowers; CYP71D351 (isoform T16H2) has a major role in the biosynthesis of vindoline in leaves
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2,3-dihydro-3-hydroxytabersonine + NADPH + H+ + O2
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low activity
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2,3-dihydrotabersonine + NADPH + H+ + O2
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low activity
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
additional information
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
highest activity
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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NADH is less active as substrate
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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first step in vindoline boxynthesis
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
indole alkaloid synthesis
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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step in monoterpenoid indole alkaloid biosynthesis, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview
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additional information
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alkaloid and enzymatic profiling of the vindoline biosynthetic pathway, overview
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additional information
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the enzyme is involved in biosynthesis of precursors in the vindoline pathway in Catharanthus roseus leaf epidermal cells, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview
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additional information
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no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine
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2,3-dihydro-3-hydroxytabersonine + NADPH + H+ + O2
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C0KYN4
low activity
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2,3-dihydrotabersonine + NADPH + H+ + O2
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C0KYN4
low activity
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
additional information
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
highest activity
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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first step in vindoline boxynthesis
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
P98183
indole alkaloid synthesis
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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step in monoterpenoid indole alkaloid biosynthesis, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview
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additional information
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alkaloid and enzymatic profiling of the vindoline biosynthetic pathway, overview
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additional information
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the enzyme is involved in biosynthesis of precursors in the vindoline pathway in Catharanthus roseus leaf epidermal cells, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview
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additional information
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C0KYN4
no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine
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cytochrome P450
K
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clotrimazole
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50% inhibition at 0.05 mM
CO
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concentration dependent competitive inhibition, 77% inhibition at 90%
cytochrome c
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50% inhibition at 0.001 mM
miconazole
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50% inhibition at 0.3 mM
tabersonine
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inhibition above 0.03 mM
tricliphane
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50% inhibition at 0.5 mM
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0.00007 - 0.011
tabersonine
0.00007
tabersonine
isoform T16H2, at pH 8.0 and 30°C
0.00035
tabersonine
isoform T16H1, at pH 8.0 and 30°C
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8
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Tris buffer
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predominantly
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isoform T16H1, CYP71D351
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highest expression of isoform T16H2, CYP71D12 in young leaves
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quantitative expression analysis in leaves
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young
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additional information
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localization study
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additional information
CYP71D12 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds; CYP71D351 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds
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T16H is anchored to the endoplasmic reticulum as a monomer via a putative 18-residue N-terminal helix
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additional information
vindoline biosynthesis pathway enzyme subcellular localization study, overview
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CYP71D351 (isoform T16H2)
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DNA and amino acid sequence determination and analysis
expressed in Saccharomyces cerevisiae WAT11 cells
T16H expression analysis in leaves, overview, recombinant expression in Escherichia coli
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C71DC_CATRO
495
56590
Swiss-Prot
U5HKE8_CATRO
512
58483
TrEMBL
C0KYN4_CATRO
506
58079
TrEMBL
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Schroder, G.; Unterbusch, E.; Kaltenbach, M.; Schmidt, J.; Strack, D.; De Luca, V.; Schroder, J.
Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase
FEBS Lett.
458
97-102
1999
Catharanthus roseus, Catharanthus roseus (P98183)
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St-Pierre, B.; De Luca, V.
A cytochrome P-450 monooxygenase catalyzes the first step in the conversion of tabersonine to vindoline in Catharanthus roseus
Plant Physiol.
109
131-139
1995
Catharanthus roseus
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Murata, J.; De Luca, V.
localization of tabersonine 16-hydroxylase and 16-OH tabersonine-16-O-methyltransferase to leaf epidermal cells defines them as a major site of precursor biosynthesis in the vindoline pathway in Catharanthus roseus
Plant J.
44
581-594
2005
Catharanthus roseus
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Magnotta, M.; Murata, J.; Chen, J.; De Luca, V.
Identification of a low vindoline accumulating cultivar of Catharanthus roseus (L.) G. Don by alkaloid and enzymatic profiling
Phytochemistry
67
1758-1764
2006
Catharanthus roseus
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Guirimand, G.; Guihur, A.; Poutrain, P.; Hericourt, F.; Mahroug, S.; St-Pierre, B.; Burlat, V.; Courdavault, V.
Spatial organization of the vindoline biosynthetic pathway in Catharanthus roseus
J. Plant Physiol.
168
549-557
2010
Catharanthus roseus (C0KYN4), Catharanthus roseus
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Besseau, S.; Kellner, F.; Lanoue, A.; Thamm, A.M.; Salim, V.; Schneider, B.; Geu-Flores, F.; Hoefer, R.; Guirimand, G.; Guihur, A.; Oudin, A.; Glevarec, G.; Foureau, E.; Papon, N.; Clastre, M.; Giglioli-Guivarch, N.; St-Pierre, B.; Werck-Reichhart, D.; Burlat, V.; De Luca, V.; OConnor, S.E.; Cou, C.o.u.r.
A pair of tabersonine 16-hydroxylases initiates the synthesis of vindoline in an organ-dependent manner in Catharanthus roseus
Plant Physiol.
163
1792-1803
2013
Catharanthus roseus (C0KYN4), Catharanthus roseus
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