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Information on EC 1.14.11.20 - deacetoxyvindoline 4-hydroxylase and Organism(s) Catharanthus roseus and UniProt Accession O04847

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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.
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This record set is specific for:
Catharanthus roseus
UNIPROT: O04847
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The taxonomic range for the selected organisms is: Catharanthus roseus
The enzyme appears in selected viruses and cellular organisms
Synonyms
desacetoxyvindoline 4-hydroxylase, desacetoxyvindoline-4-hydroxylase, deacetoxyvindoline 4-hydroxylase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
deacetoxyvindoline 4-hydroxylase
-
desacetoxyvindoline 4-hydroxylase
-
desacetoxyvindoline-4-hydroxylase
-
desacetoxyvindoline-4-hydroxylase
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
deacetoxyvindoline + 2-oxoglutarate + O2 = deacetylvindoline + succinate + CO2
show the reaction diagram
ordered Ter Ter mechanism is suggested, deacetylvindoline is the first product released, followed by CO2 and succinate
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
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.
CAS REGISTRY NUMBER
COMMENTARY hide
132084-83-4
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
deacetoxyvindoline + 2-oxoglutarate + O2
deacetylvindoline + succinate + CO2
show the reaction diagram
deacetoxyvindoline + 2-oxoglutarate + O2
deacetylvindoline + succinate + CO2
show the reaction diagram
-
-
-
-
?
desacetoxyvindoline + 2-oxoglutarate + O2
desacetylvindoline + succinate + CO2
show the reaction diagram
-
strictly specific for position 4, no hydroxylation of indole alkaloid substrates with a 2,3-double bond
-
?
additional information
?
-
-
the desacetoxyvindoline-4-hydroxylase interacts with the deacetylvindoline-4-O-acetyltransferase, analysis via yeast two-hybrid system
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
deacetoxyvindoline + 2-oxoglutarate + O2
deacetylvindoline + succinate + CO2
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
the desacetoxyvindoline-4-hydroxylase interacts with the deacetylvindoline-4-O-acetyltransferase, analysis via yeast two-hybrid system
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-oxoglutarate
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CO
-
7.5 mM, 50% inhibition
desacetylvindoline
-
product inhibition, noncompetitive vs. 2-oxoglutarate
succinate
-
product inhibition, competitive vs. 2-oxoglutarate, noncompetitive vs. desacetoxyvindoline
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbic acid
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.045
2-oxoglutarate
-
-
0.2
ascorbate
-
-
0.000003
desacetoxyvindoline
-
-
0.0085
Fe2+
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.115
deacetylvindoline
-
-
9
succinate
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00012
continuous light, day 0, 4 and 8
0.00015
day 32 and 36, continuous light
0.0003
day 28, continuous light
0.00036
day 36, photoperiod
0.0006
0.0009
day 8, photoperiod
0.0012
0.0015
0.0016
day 16, photoperiod
0.0018
day 12, photoperiod
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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
Manually annotated by BRENDA team
no association between plantlet formation and other biosynthetic enzymes such as deacetoxyvindoline 4-hydroxylase and tryptophan decarboxylase, is found
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
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
Manually annotated by BRENDA team
additional information
-
vindoline biosynthesis pathway enzyme subcellular localization study, overview
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
part of vindoline biosynthesis
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
DV4H_CATRO
401
0
45647
Swiss-Prot
Chloroplast (Reliability: 5)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45647
* 45647, calculated
44700
-
1 * 44700, SDS-PAGE
45000
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
* 45647, calculated
monomer
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Sephadex G-100, Green 19-agarose, hydroxylapatite, 2-oxoglutarate-Sepharose, Mono-Q
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloning of cDNA, expression in Escherichia coli, possibly dimorphic allele of a single-copy gene
cloning of cDNA, possibly dimorphic allele of a single-copy gene
gene D4H, semi-quantitative RT-PCR expression analysis
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
artemisinic acid is able to upregulate the transcriptions of deacetoxyvindoline 4-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
upregulated in plants inoculated with endophytes
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
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
artemisinic acid can be used as a promising elicitor, especially for the production of therapeutically important indole alkaloids
synthesis
-
maximal production of vindoline coincides with maximal activity of enzyme and of deacetylvindoline acetyl-CoA acetyl transferase and tryptophan decarboxylase
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
-
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team