Information on EC 1.3.99.27 - 1-hydroxycarotenoid 3,4-desaturase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.99.27
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RECOMMENDED NAME
GeneOntology No.
1-hydroxycarotenoid 3,4-desaturase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
1-hydroxy-1,2-dihydrolycopene + acceptor = 1-hydroxy-3,4-didehydro-1,2-dihydrolycopene + reduced acceptor
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Carotenoid biosynthesis
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Metabolic pathways
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spirilloxanthin and 2,2'-diketo-spirilloxanthin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
1-hydroxy-1,2-dihydrolycopene:acceptor oxidoreductase
The enzymes from Rubrivivax gelatinosus and Rhodobacter sphaeroides prefer the acyclic carotenoids (e.g. 1-hydroxy-1,2-dihydroneurosporene, 1-hydroxy-1,2-dihydrolycopene) as substrates. The conversion rate for the 3,4-desaturation of the monocyclic 1'-hydroxy-1',2'-dihydro-gamma-carotene is lower [2,3]. The enzyme from the marine bacterium strain P99-3 shows high activity with the monocyclic carotenoid 1'-hydroxy-1',2'-dihydro-gamma-carotene [1]. The enzyme from Rhodobacter sphaeroides utilizes molecular oxygen as the electron acceptor in vitro [3]. However, oxygen is unlikely to be the natural electron acceptor under anaerobic conditions.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
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the deletion mutant shows a different carotenoid pattern than the wild-type enzyme
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1'-hydroxy-gamma-carotene + acceptor
1'-hydroxytorulene + reduced acceptor
show the reaction diagram
1,1'-dihydroxy-3,4-didehydrolycopene + acceptor
1,1'-dihydroxy-3,4,3',4'-tetradehydrolycopene + reduced acceptor
show the reaction diagram
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38% conversion
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?
1,1'-dihydroxyneurosporene + acceptor
1'-hydroxy-1-demethylspheroidene + reduced acceptor
show the reaction diagram
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39% conversion
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?
1-hydroxy-1,2-dihydrorhodopin + acceptor
1-hydroxy-3,4-didehydro-1,2-dihydrorhodopin + reduced acceptor
show the reaction diagram
1-hydroxy-3',4'-didehydrolycopene + acceptor
1-hydroxy-3,4,3',4'-tetradehydrolycopene + reduced acceptor
show the reaction diagram
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28% conversion
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?
1-hydroxy-3,4-didehydrolycopene + acceptor
1-hydroxy-3,4,3'-4'-tetradehydrolycopene + reduced acceptor
show the reaction diagram
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?
1-hydroxy-zeta-carotene + acceptor
1-hydroxy-3,4-didehydro-zeta-carotene + reduced acceptor
show the reaction diagram
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15% conversion
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?
1-hydroxylycopene + acceptor
1-hydroxy-3,4-didehydrolycopene + reduced acceptor
show the reaction diagram
1-hydroxyneurosporene + acceptor
1-demethylspheroidene + reduced acceptor
show the reaction diagram
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47% conversion. The 3,4-desaturation reaction can only occur with mono-1-hydroxy carotenoids at a Psi-end group or with 1,1'-dihydroxy derivatives carrying a 3'4'-double bond. In addition, 1-hydroxy-zeta-carotene could also be converted by the desaturase. Enzyme kinetic studies show a substrate preference of 1-hydroxyneurosporene over 1-hydroxylycopene
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?
1-hydroxyneurosporene + acceptor
demethylspheroidene + reduced acceptor
show the reaction diagram
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when O2 is depleted less than 10% of the specific actvity is retained. It is rather unlikely that molecular oxygen is the genuine cofactor for hydroxyneurosporene desaturation reactions in Rhodobacter cells when they reach their maximum carotenoid content under anaerobic conditions. Consequently, another, as-yet-unknown electron acceptor may exist in Rhodobacter species that replaces molecular oxygen during anaerobic growth
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?
1-methoxy-1'-hydroxy-3,4-didehydrolycopene + acceptor
1-methoxy-1'-hydroxy-3,4,3',4'-tetradehydrolycopene + reduced acceptor
show the reaction diagram
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37% conversion
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1'-hydroxy-gamma-carotene + acceptor
1'-hydroxytorulene + reduced acceptor
show the reaction diagram
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the enzyme is involved in myxol biosynthesis
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?
1-hydroxy-1,2-dihydrorhodopin + acceptor
1-hydroxy-3,4-didehydro-1,2-dihydrorhodopin + reduced acceptor
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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NAD+, NADP+, and flavin adenine dinucleotide have no influence on enzymatic activity. When O2 is depleted less than 10% of the specific actvity is retained. It is rather unlikely that molecular oxygen is the genuine cofactor for hydroxyneurosporene desaturation reactions in Rhodobacter cells when they reach their maximum carotenoid content under anaerobic conditions. Consequently, another, as-yet-unknown electron acceptor may exist in Rhodobacter species that replaces molecular oxygen during anaerobic growth
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.019
1,1'-dihydroxyneurosporene
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pH 7.8, 28°C
0.04
1-hydroxylycopene
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pH 7.8, 28°C
0.0134 - 0.025
1-hydroxyneurosporene
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55000
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x * 55000, calculated from sequence
58000
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x * 58000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expression in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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heterologous production of two unusual acyclic carotenoids, 1,1'-dihydroxy-3,4-didehydrolycopene and 1-hydroxy-3,4,3',4'-tetradehydrolycopene by combination of the crtC and crtD genes from Rhodobacter and Rubrivivax