Information on EC 1.3.1.99 - iridoid synthase

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The expected taxonomic range for this enzyme is: Catharanthus roseus

EC NUMBER
COMMENTARY hide
1.3.1.99
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RECOMMENDED NAME
GeneOntology No.
iridoid synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(6E)-8-oxogeranial + NAD(P)H + H+ = cis-trans-nepetalactol + NAD(P)+
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
8-oxogeranial:NAD(P)+ oxidoreductase (cyclizing, cis-trans-nepetalactol forming)
Isolated from the plant Catharanthus roseus. The reaction may involve cyclization via a Diels-Alder or Michael reaction. Iridoids are involved in the biosynthesis of many indole alkaloids. The cyclic hemiacetal is readily hydrolysed to the corresponding dial.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-10-oxocitronellal + NAD(P)H + H+
?
show the reaction diagram
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about 10% activity compared to 10-oxogeranial
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ir
(S)-10-oxocitronellal + NAD(P)H + H+
?
show the reaction diagram
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less than 5% activity compared to 10-oxogeranial
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ir
10-oxogeranial + NADH + H+
cis-trans-nepetalactol + NAD+
show the reaction diagram
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100% activity
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ir
10-oxogeranial + NADPH + H+
cis-trans-nepetalactol + NADP+
show the reaction diagram
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100% activity
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ir
10-oxogeraniol + NAD(P)H + H+
?
show the reaction diagram
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less than 10% activity compared to 10-oxogeranial
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ir
6,7-dihydro-10-oxogeranial + NAD(P)H + H+
?
show the reaction diagram
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about 25% activity compared to 10-oxogeranial
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ir
citral + NAD(P)H + H+
?
show the reaction diagram
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about 90% activity compared to 10-oxogeranial
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ir
additional information
?
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no activity with (S)-10-oxocitronellal, (S)-citronellal, and (R)-citronellal
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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