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Information on EC 1.14.11.20 - deacetoxyvindoline 4-hydroxylase
for references in articles please use BRENDA:EC1.14.11.20
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.11 With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
1.14.11.20 deacetoxyvindoline 4-hydroxylase
IUBMB Comments
Requires Fe2+ and ascorbate. Also acts on 3-hydroxy-16-methoxy-2,3-dihydrotabersonine and to a lesser extent on 16-methoxy-2,3-dihydrotabersonine.
The enzyme appears in viruses and cellular organisms
- 1.14.11.20
- roseus
- catharanthus
- indole
-
terpenoid
- strictosidine
- vinblastine
- jasmonate
- deacetylvindoline
- vincristine
- elicitors
- periwinkle
- tabersonine
- geraniol
-
madagascar
- shoot
-
monoterpenoid
-
artemisinic
-
16-hydroxylase
-
catharanthine
-
etiolated
-
ap2-domain
-
aerial
- idioblasts
-
2-oxoglutarate-dependent
-
suspension-cultured
-
sixfold
- ajmalicine
- synthesis
- laticifer
-
dark-grown
-
1.14.11.11
Reaction Schemes
showSynonyms
desacetoxyvindoline 4-hydroxylase, desacetoxyvindoline-4-hydroxylase, deacetoxyvindoline 4-hydroxylase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
D4H
desacetoxyvindoline-4-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
deacetoxyvindoline + 2-oxoglutarate + O2 = deacetylvindoline + succinate + CO2
ordered Ter Ter mechanism is suggested, deacetylvindoline is the first product released, followed by CO2 and succinate
-
deacetoxyvindoline + 2-oxoglutarate + O2 = deacetylvindoline + succinate + CO2
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
vindoline, vindorosine and vinblastine biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
deacetoxyvindoline,2-oxoglutarate:oxygen oxidoreductase (4beta-hydroxylating)
Requires Fe2+ and ascorbate. Also acts on 3-hydroxy-16-methoxy-2,3-dihydrotabersonine and to a lesser extent on 16-methoxy-2,3-dihydrotabersonine.
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CAS REGISTRY NUMBER
COMMENTARY
132084-83-4
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
desacetoxyvindoline + 2-oxoglutarate + O2
desacetylvindoline + succinate + CO2
-
Substrates: strictly specific for position 4, no hydroxylation of indole alkaloid substrates with a 2,3-double bond
Products: -
Products: -
?
additional information
?
-
-
Substrates: the desacetoxyvindoline-4-hydroxylase interacts with the deacetylvindoline-4-O-acetyltransferase, analysis via yeast two-hybrid system
Products: -
Products: -
?
deacetoxyvindoline + 2-oxoglutarate + O2
deacetylvindoline + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
deacetoxyvindoline + 2-oxoglutarate + O2
deacetylvindoline + succinate + CO2
Substrates: -
Products: -
Products: -
?
deacetoxyvindoline + 2-oxoglutarate + O2
deacetylvindoline + succinate + CO2
Substrates: -
Products: -
Products: -
ir
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
deacetoxyvindoline + 2-oxoglutarate + O2
deacetylvindoline + succinate + CO2
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: the desacetoxyvindoline-4-hydroxylase interacts with the deacetylvindoline-4-O-acetyltransferase, analysis via yeast two-hybrid system
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
desacetylvindoline
-
product inhibition, noncompetitive vs. 2-oxoglutarate
succinate
-
product inhibition, competitive vs. 2-oxoglutarate, noncompetitive vs. desacetoxyvindoline
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0006
0.0012
0.0015
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
different isoforms in etiolated and light-grown seedlings
SwissProt
brenda
no association between plantlet formation and other biosynthetic enzymes such as deacetoxyvindoline 4-hydroxylase and tryptophan decarboxylase, is found
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
no association between plantlet formation and other biosynthetic enzymes such as deacetoxyvindoline 4-hydroxylase and tryptophan decarboxylase, is found
brenda
etiolated seed, contains considerable levels of transcript but almost undetectable enzymic activity. Exposure of seedlings to light results in a rapid increase of enzyme activity without a significant further increase in d4h transcripts over those detected in dark-grown seedlings
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
the enzyme resides in the nucleocytoplasmic compartment following passive diffusion to the nucleus allowed by the protein size. Colocalization with deacetylvindoline-4-O-acetyltransferase
brenda
additional information
-
vindoline biosynthesis pathway enzyme subcellular localization study, overview
-
brenda
Highest Expressing Human Cell Lines
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
metabolism
-
the enzyme catalyzes the penultimate 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. The desacetoxyvindoline-4-hydroxylase interacts directly with the deacetylvindoline-4-O-acetyltransferase, that catalyzes the last step of the biosynthetic pathway, 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
the enzyme is involved in biosynthesis of terpenoidindole alkaloids
metabolism
the enzyme is involved in terpenoid indole alkaloid (TIA) biosynthetic pathway
Show AA Sequence and Transmembrane Helices (169 entries)
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
45000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Sephadex G-100, Green 19-agarose, hydroxylapatite, 2-oxoglutarate-Sepharose, Mono-Q
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloning of cDNA, expression in Escherichia coli, possibly dimorphic allele of a single-copy gene
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
artemisinic acid is able to upregulate the transcriptions of deacetoxyvindoline 4-hydroxylase
artemisinic acid leads to upregulation of the deacetoxyvindoline 4-hydroxylase and upstream enzymes of the vinblastine biosynthesis, i.e. tryptophan decarboxylase, geraniol 10-hydroxylase, tabersonine 16-hydroxylase
-
significant upregulation in salicylic acid treatment (foliar application of 0.01 and 0.1 mM salicylic acid). Upregulation can result in a higher production rate of vinblastine and vincristine alkaloids
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
maximal production of vindoline coincides with maximal activity of enzyme and of deacetylvindoline acetyl-CoA acetyl transferase and tryptophan decarboxylase
synthesis
artemisinic acid can be used as a promising elicitor, especially for the production of therapeutically important indole alkaloids
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
De Carolis, E.; Chan, F.; Balsevich, J.; De Luca, V.
Isolation and characterization of a 2-oxoglutarate dependent dioxygenase involved in the second-to-last step in vindoline biosynthesis
Plant Physiol.
94
1323-1329
1990
Catharanthus roseus
brenda
De Carolis, E.; De Luca, V.
Purification, characterization, and kinetic analysis of a 2-oxoglutarate-dependent dioxygenase involved in vindoline biosynthesis from Catharanthus roseus
J. Biol. Chem.
268
5504-5511
1993
Catharanthus roseus
brenda
Carolis, E.D.; Luca, V.D.
A novel 2-oxoglutarate-dependent dioxygenase involved in vindoline biosynthesis: Characterization, purification and kinetic properties
Plant Cell Tissue Organ Cult.
38
281-287
1994
Catharanthus roseus
-
brenda
Vazquez-Flota, F.; De Carolis, E.; Alarco, A.M.; De Luca, V.
Molecular cloning and characterization of desacetoxyvindoline-4-hydroxylase, a 2-oxoglutarate dependent-dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don
Plant Mol. Biol.
34
935-948
1997
Catharanthus roseus (O04847), Catharanthus roseus
brenda
Vazquez-Flota, F.A.; De Luca, V.
Developmental and light regulation of desacetoxyvindoline 4-hydroxylase in Catharanthus roseus (L.) G. Don. Evidence of a multilevel regulatory mechanism
Plant Physiol.
117
1351-1361
1998
Catharanthus roseus (O04847), Catharanthus roseus
brenda
Hernandez-Dominguez, E.; Campos-Tamayo, F.; Vazquez-Flota, F.
Vindoline synthesis in in vitro shoot cultures of Catharanthus roseus
Biotechnol. Lett.
26
671-674
2004
Catharanthus roseus
brenda
Dutta, A.; Batra, J.; Pandey-Rai, S.; Singh, D.; Kumar, S.; Sen, J.
Expression of terpenoid indole alkaloid biosynthetic pathway genes corresponds to accumulation of related alkaloids in Catharanthus roseus (L.) G. Don
Planta
220
376-383
2005
Catharanthus roseus (O04847), Catharanthus roseus
brenda
Campos-Tamayo, F.; Hernandez-Dominguez, E.; Vazquez-Flota, F.
Vindoline formation in shoot cultures of Catharanthus roseus is synchronously activated with morphogenesis through the last biosynthetic step
Ann. Bot.
102
409-415
2008
Catharanthus roseus, Catharanthus roseus (O04847)
brenda
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
brenda
Liu, J.; Zhu, J.; Tang, L.; Wen, W.; Lv, S.; Yu, R.
Enhancement of vindoline and vinblastine production in suspension-cultured cells of Catharanthus roseus by artemisinic acid elicitation
World J. Microbiol. Biotechnol.
30
175-180
2013
Catharanthus roseus
brenda
Pandey, S.S.; Singh, S.; Babu, C.S.; Shanker, K.; Srivastava, N.K.; Shukla, A.K.; Kalra, A.
Fungal endophytes of Catharanthus roseus enhance vindoline content by modulating structural and regulatory genes related to terpenoid indole alkaloid biosynthesis
Sci. Rep.
6
26583
2016
Catharanthus roseus (O04847), Catharanthus roseus
brenda
Liu, J.; Zhu, J.; Tang, L.; Wen, W.; Lv, S.; Yu, R.
Enhancement of vindoline and vinblastine production in suspension-cultured cells of Catharanthus roseus by artemisinic acid elicitation
World J. Microbiol. Biotechnol.
30
175-180
2014
Catharanthus roseus (O04847), Catharanthus roseus
brenda
Soltani, N.; Nazarian-Firouzabadi, F.; Shafeinia, A.; Sadr, A.S.; Shirali, M.
The expression of terpenoid indole alkaloid (TIAs) pathway genes in Catharanthus roseus in response to salicylic acid treatment
Mol. Biol. Rep.
47
7009-7016
2020
Catharanthus roseus (O04847), Catharanthus roseus
brenda
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