Information on EC 2.3.1.150 - Salutaridinol 7-O-acetyltransferase

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The expected taxonomic range for this enzyme is: Papaver

EC NUMBER
COMMENTARY hide
2.3.1.150
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RECOMMENDED NAME
GeneOntology No.
Salutaridinol 7-O-acetyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + salutaridinol = CoA + 7-O-acetylsalutaridinol
show the reaction diagram
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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Isoquinoline alkaloid biosynthesis
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Metabolic pathways
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morphine biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
acetyl-CoA:salutaridinol 7-O-acetyltransferase
The enzyme is present in the poppy, Papaver somniferum. At pH 8-9 the product, 7-O-acetylsalutaridinol, spontaneously closes the 4->5 oxide bridge by allylic elimination to form the morphine precursor thebaine
CAS REGISTRY NUMBER
COMMENTARY hide
156859-13-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
no activity in Papaver rhoeas
cell cultures
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Papaver sp.
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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SalAT is involved in the benzylisoquinoline alkaloid biosynthesis in opium poppy from (R)-reticuline to morphine, pathway overview
physiological function
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yeast two-hybrid and co-immunoprecipitation analyses indicate an interaction between salutaridine reductase and SalAT, which suggest the occurrence of an enzyme complex
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
Acetyl-CoA + nudaurine
?
show the reaction diagram
-
-
-
-
-
acetyl-CoA + nudaurine
CoA + O-acetylnudaurine
show the reaction diagram
-
-
-
?
Acetyl-CoA + salutaridinol
?
show the reaction diagram
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
show the reaction diagram
n-Hexanoyl-CoA + salutaridinol
?
show the reaction diagram
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-
-
-
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n-Propionyl-CoA + salutaridinol
?
show the reaction diagram
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-
-
-
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salutaridinol + acetyl-CoA
salutaridinol-7-O-acetate + CoA
show the reaction diagram
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morphinan pathway
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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
Acetyl-CoA + salutaridinol
?
show the reaction diagram
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
show the reaction diagram
additional information
?
-
-
yeast two-hybrid and co-immunoprecipitation analyses indicate an interaction between salutaridine reductase and SalAT, which suggest the occurrence of an enzyme complex
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-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetyl-CoA
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dependent on
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
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0.1 mM, 56% inhibition
8-hydroxyquinoline
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0.1 mM, 85% inhibition
Cd2+
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1 mM, strong
codeinone
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0.5 mM, 55% inhibition
Cu2+
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1 mM, strong
Diethyldicarbamate
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0.05 mM, 87% inhibition
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p-chloromercuribenzoate
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weak
salutaridine
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0.5 mM, 74% inhibition
thebaine
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0.5 mM, 76% inhibition
Zn2+
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1 mM, strong
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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increased enzyme level after treatment with extracts from Botrytis sp.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.046 - 0.106
acetyl-CoA
0.093
n-Hexanoyl-CoA
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0.068
n-propionyl-CoA
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0.023
nudaurine
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0.007 - 0.009
salutaridinol
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.3
nudaurine
Papaver somniferum
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4.4
salutaridinol
Papaver somniferum
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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high enzyme level
Manually annotated by BRENDA team
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enzyme protein is restricted to sieve elements of the phloem adjacent or proximal to laticifers. Corresponding gene transcripts are found in the companion cell paired with each sieve element
Manually annotated by BRENDA team
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increasing enzyme level in developing seedlings
Manually annotated by BRENDA team
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in developing root tips
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
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1 * 50000, SDS-PAGE
52600
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x * 52600, calculated from the deduced amino acid sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purification from host organism and recombinant protein using His-tag
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using affinity chromatography and gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Agrobacterium-mediated transfection of Papaver somniferum with the salutaridinol 7-O-acetyltransferase gene, 21 transgenic opium poppy plants over-expressing SalAT are analysed in three separate glasshouse trials, suppression of SalAT by RNAi, SalAT involved in alkaloid accumulation
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expressed as His-tag fusion protein in Sf9 insect cells
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expressed in Escherichia coli as a His-tagged fusion protein
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real-time quantitative PCR expression analysis
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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specific gene silencing of the enzymes involved in alkaloid biosynthesis in opium poppy using virus-induced gene silencing, VIGS, and Agrobacterium tumefaciens transfection
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
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increases in pharmaceutical alkaloid content of potential economic significance have been achieved, RNAi suppression is a powerful way to obtain products that poppy does not normally accumulate
synthesis