Information on EC 2.2.1.12 - 3-acetyloctanal synthase

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The expected taxonomic range for this enzyme is: Serratia

EC NUMBER
COMMENTARY hide
2.2.1.12
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RECOMMENDED NAME
GeneOntology No.
3-acetyloctanal synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
pyruvate + (E)-oct-2-enal = (S)-3-acetyloctanal + CO2
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
prodigiosin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
pyruvate:(E)-oct-2-enal acetaldehydetransferase (decarboxylating)
Requires thiamine diphosphate. The enzyme, characterized from the bacterium Serratia marcescens, participates in the biosynthesis of the antibiotic prodigiosin. The enzyme decarboxylates pyruvate, followed by attack of the resulting two-carbon fragment on (E)-oct-2-enal, resulting in a Stetter reaction. In vitro the enzyme can act on a number of alpha,beta-unsaturated carbonyl compounds, including aldehydes and ketones, and can catalyse both 1-2 and 1-4 carboligations depending on the substrate.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-oxobutanoate + (3E)-4-(4-chlorophenyl)but-3-en-2-one
?
show the reaction diagram
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?
pyruvate + (2E)-1,3-diphenylprop-2-en-1-one
(3R)-1,3-diphenylpentane-1,4-dione + CO2
show the reaction diagram
the PigD-catalyzed reaction yields 3% 1,4-carboligation product, with an enantiomeric excess above 99%
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?
pyruvate + (2E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
(3R)-3-(2-hydroxyphenyl)-1-phenylpentane-1,4-dione + CO2
show the reaction diagram
the PigD-catalyzed reaction yields 39% 1,4-carboligation product, with an enantiomeric excess above 99%
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?
pyruvate + (2E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
(3R)-3-(4-methoxyphenyl)-1-phenylpentane-1,4-dione + CO2
show the reaction diagram
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?
pyruvate + (3E)-4-(4-chlorophenyl)but-3-en-2-one
(3R)-3-(4-chlorophenyl)hexane-2,5-dione + CO2
show the reaction diagram
pyruvate + (3E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
(3R)-3-(4-hydroxy-3-methoxyphenyl)hexane-2,5-dione + CO2
show the reaction diagram
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?
pyruvate + (3E)-4-(furan-2-yl)but-3-en-2-one
(3R)-3-(furan-2-yl)hexane-2,5-dione + CO2
show the reaction diagram
10% conversion
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?
pyruvate + (3E)-4-(furan-2-yl)but-3-en-2-one
3-(furan-2-yl)hexane-2,5-dione + CO2
show the reaction diagram
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11% conversion
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?
pyruvate + (3E)-4-(thiophen-2-yl)but-3-en-2-one
(3S)-3-(thiophen-2-yl)hexane-2,5-dione + CO2
show the reaction diagram
15% conversion
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?
pyruvate + (3E)-4-phenylbut-3-en-2-one
(3R)-3-phenylhexane-2,5-dione + CO2
show the reaction diagram
pyruvate + (3E)-dec-3-en-2-one
(3S)-3-hexylhexane-2,5-dione + CO2
show the reaction diagram
the PigD-catalyzed reaction yields 30% 1,4-carboligation product, with an enantiomeric excess above 99%
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?
pyruvate + (3E)-non-3-en-2-one
(3S)-3-pentylhexane-2,5-dione + CO2
show the reaction diagram
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
show the reaction diagram
pyruvate + 3-phenylbut-3-en-2-one
(3R)-3-phenylhexane-2,5-dione + CO2
show the reaction diagram
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?
pyruvate + but-3-en-2-one
hexane-2,5-dione + CO2
show the reaction diagram
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8% conversion
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?
pyruvate + S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate
S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate + CO2
show the reaction diagram
highest conversion of all tested substrates into the 1,4-addition product
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?
pyruvate + S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate
S-[2-(acetylamino)ethyl] 3-acetyloctanethioate + CO2
show the reaction diagram
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75% conversion
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additional information
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PigD catalyzes 1,2-additions using 2-oxoacids as donor substrates and aldehydes as acceptors. In the case of ketones as acceptors PigD catalyzes the 1,4-addition. Although pyruvate is the preferred donor substrate, 2-oxobutanoate is also employed using (E)-4-(4-chlorophenyl)-but-3-en-2-one as an acceptor
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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
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
thiamine diphosphate
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
the gene is cloned the gene with an attached hexahistidine (His6) tag at the C terminus
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