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Information on EC 2.3.1.150 - Salutaridinol 7-O-acetyltransferase and Organism(s) Papaver somniferum and UniProt Accession Q94FT4
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2.3.1.150 Salutaridinol 7-O-acetyltransferaseIUBMB Comments
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
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Word Map
- 2.3.1.150
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prayer
-
muslim
- morphine
- thebaine
-
papaver
- somniferum
-
morphinans
-
recite
-
islamic
- poppy
-
posture
-
opium
-
bowing
-
prostration
-
praying
-
spiritual
-
meditation
- codeinone
-
worship
- bracteatum
- synthesis
- biotechnology
The taxonomic range for the selected organisms is: Papaver somniferum
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
salat, salutaridinol 7-o-acetyltransferase, pssat, salutaridine 7-o-acetyltransferase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Acetyl-CoA:salutaridinol-7-O-acetyltransferase
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-
-
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Acetyltransferase, salutaridinol 7-O-
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
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-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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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
156859-13-1
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
Acetyl-CoA + salutaridinol
?
-
the enzyme catalyzes the formation of thebaine in morphine biosynthesis
-
-
?
salutaridinol + acetyl-CoA
salutaridinol-7-O-acetate + CoA
-
morphinan pathway
-
-
?
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
-
-
-
?
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
involved in morphine biosynthesis
-
-
?
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
-
-
-
-
?
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
-
involved in morphine biosynthesis
-
-
?
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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-
?
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
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
involved in morphine biosynthesis
-
-
?
Acetyl-CoA + salutaridinol
?
-
the enzyme catalyzes the formation of thebaine in morphine biosynthesis
-
-
?
acetyl-CoA + salutaridinol
CoA + 7-O-acetylsalutaridinol
-
involved in morphine biosynthesis
-
-
?
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
-
-
?
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
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
increased enzyme level after treatment with extracts from Botrytis sp.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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
abundance of enzyme increases rapidly between 1 and 3 days of seed germination
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
RNA interference of salAT leads to accumulation of the intermediate compounds, salutaridine and salutaridinol. SalAT transcript is shown by quantitative PCR to be diminished, while salutaridine reductase transcript levels remains unaffected
physiological function
yeast two-hybrid and co-immunoprecipitation analyses indicate an interaction between salutaridine reductase and SalAT, which suggest the occurrence of an enzyme complex
malfunction
-
silencing of the gene encoding SalAT results in the accumulation of salutaridine, which is not the corresponding enzymatic substrate. Reduction of SalAt transcript and protein levels results in an increase in salutaridine, i.e. an approximately 20-fold increase compared with controls, and a concomitant decrease in thebaine levels. Codeine and morphine accumulation are also significantly reduced
metabolism
-
SalAT is involved in the benzylisoquinoline alkaloid biosynthesis in opium poppy from (R)-reticuline to morphine, pathway overview
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). SALAT_PAPSO
474
0
52632
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
specific gene silencing of the enzymes involved in alkaloid biosynthesis in opium poppy using virus-induced gene silencing, VIGS, and Agrobacterium tumefaciens transfection
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purification from host organism and recombinant protein using His-tag
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
salutaridine synthase (PsSAS), salutaridine reductase (PsSAR) and salutaridinol acetyltransferase (PsSAT) are functionally coexpressed in Saccharomyces cerevisiae and optimization of the pH conditions allowed for productive spontaneous rearrangement of salutaridinol-7-O-acetate and synthesis of thebaine from (R)-reticuline. A 7-gene pathway for the production of codeine and morphine from (R)-reticuline is reconstituted. Yeast cell feeding assays using (R)-reticuline, salutaridine or codeine as substrates show that all enzymes are functionally coexpressed in yeast and that activity of salutaridine reductase and codeine-O-demethylase likely limit flux to morphine synthesis. The results of this study describe a significant advance for the synthesis of morphinans in Saccharomyces cerevisiae and pave the way for their complete synthesis in recombinant microbes
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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
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
potential application in biotechnological production of morphine alkaloids
synthesis
coexpression of Papaver somniferum enzymes salutaridine synthase, salutaridine reductase and salutaridinol in Saccharomyces cerevisiae allows for productive spontaneous rearrangement of salutaridinol-7-O-acetate and synthesis of thebaine from (R)-reticuline. A 7-gene pathway for the production of codeine and morphine from (R)-reticuline can be established. Yeast cell feeding assays using (R)-reticuline, salutaridine or codeine as substrates show that all enzymes are functionally coexpressed and that activity of salutaridine reductase and codeine-O-demethylase likely limit flux to morphine synthesis
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lenz, R.; Zenk, M.H.
Acetyl coenzyme A:salutaridinol-7-O-acetyltransferase from Papaver somniferum plant cell cultures
J. Biol. Chem.
270
31091-31096
1995
no activity in Papaver rhoeas, Papaver bracteatum, Papaver somniferum
Weid, M.; Ziegler, J.; Kutchan, T.M.
The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum
Proc. Natl. Acad. Sci. USA
101
13957-13962
2004
Papaver somniferum
Facchini, P.J.; Park, S.U.
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy
Phytochemistry
64
177-186
2003
Papaver somniferum
Grothe, T.; Lenz, R.; Kutchan, T.M.
Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum
J. Biol. Chem.
276
30717-30723
2001
Papaver somniferum (Q94FT4), Papaver somniferum
Samanani, N.; Alcantara, J.; Bourgault, R.; Zulak, K.G.; Facchini, P.J.
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy
Plant J.
47
547-563
2006
Papaver somniferum (Q94FT4)
Allen, R.S.; Miller, J.A.; Chitty, J.A.; Fist, A.J.; Gerlach, W.L.; Larkin, P.J.
Metabolic engineering of morphinan alkaloids by over-expression and RNAi suppression of salutaridinol 7-O-acetyltransferase in opium poppy
Plant Biotechnol. J.
6
22-30
2008
Papaver somniferum
Kempe, K.; Higashi, Y.; Frick, S.; Sabarna, K.; Kutchan, T.M.
RNAi suppression of the morphine biosynthetic gene salAT and evidence of association of pathway enzymes
Phytochemistry
70
579-589
2009
Papaver somniferum (Q94FT4), Papaver somniferum
Wijekoon, C.P.; Facchini, P.J.
Systematic knockdown of morphine pathway enzymes in opium poppy using virus-induced gene silencing
Plant J.
69
1052-1063
2012
Papaver somniferum
Fossati, E.; Narcross, L.; Ekins, A.; Falgueyret, J.P.; Martin, V.J.
Synthesis of morphinan alkaloids in Saccharomyces cerevisiae
PLoS ONE
10
e0124459
2015
Papaver somniferum (Q94FT4)
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