Information on EC 1.14.15.12 - pimeloyl-[acyl-carrier protein] synthase

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The expected taxonomic range for this enzyme is: Bacillus subtilis

EC NUMBER
COMMENTARY hide
1.14.15.12
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RECOMMENDED NAME
GeneOntology No.
pimeloyl-[acyl-carrier protein] synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a (7R,8R)-7,8-dihydroxy-long-chain-acyl-[acyl-carrier protein] + reduced flavodoxin + O2 = a 7-oxoheptanoyl-[acyl-carrier protein] + an n-alkanal + oxidized flavodoxin + 2 H2O
show the reaction diagram
a (7S)-7-hydroxy-long-chain-acyl-[acyl-carrier protein] + reduced flavodoxin + O2 = a (7R,8R)-7,8-dihydroxy-long-chain-acyl-[acyl-carrier protein] + oxidized flavodoxin + H2O
show the reaction diagram
a 7-oxoheptanoyl-[acyl-carrier protein] + oxidized flavodoxin + H2O = a pimeloyl-[acyl-carrier protein] + reduced flavodoxin + H+
show the reaction diagram
a long-chain acyl-[acyl-carrier protein] + 2 reduced flavodoxin + 3 O2 = pimeloyl-[acyl-carrier protein] + an n-alkanal + 2 oxidized flavodoxin + 3 H2O
show the reaction diagram
a long-chain acyl-[acyl-carrier protein] + reduced flavodoxin + O2 = a (7S)-7-hydroxy-long-chain-acyl-[acyl-carrier protein] + oxidized flavodoxin + H2O
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biotin metabolism
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SYSTEMATIC NAME
IUBMB Comments
acyl-[acyl-carrier protein],reduced-flavodoxin:oxygen oxidoreductase (pimeloyl-[acyl-carrier protein] forming)
A heme-thiolate protein (P-450). The enzyme catalyses an oxidative C-C bond cleavage of long-chain acyl-[acyl-carrier protein]s of various lengths to generate pimeloyl-[acyl-carrier protein], an intermediate in the biosynthesis of biotin. The preferred substrate of the enzyme from the bacterium Bacillus subtilis is palmitoyl-[acyl-carrier protein] which then gives heptanal as the alkanal. The mechanism is similar to EC 1.14.15.6, cholesterol monooxygenase (side-chain-cleaving), followed by a hydroxylation step, which may occur spontaneously [2].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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
(7R,8R)-7,8-dihydroxytetradecanoyl-[acyl carrier protein] + reduced flavodoxin + O2
pimeloyl-[acyl-carrier protein] + ?
show the reaction diagram
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best substrate
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?
(7R,8S)-7,8-dihydroxytetradecanoyl-[acyl carrier protein] + reduced flavodoxin + O2
pimeloyl-[acyl-carrier protein] + ?
show the reaction diagram
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-
-
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?
7-hydroxytetradecanoyl-[acyl carrier protein] + reduced flavodoxin + O2
pimeloyl-[acyl-carrier protein] + ?
show the reaction diagram
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-
-
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?
7-oxotetradecanoyl-[acyl carrier protein] + reduced flavodoxin + O2
pimeloyl-[acyl-carrier protein] + ?
show the reaction diagram
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-
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?
a long-chain acyl-[acyl-carrier protein] + reduced flavodoxin + O2
pimeloyl-[acyl-carrier protein] + an n-alkanal + oxidized flavodoxin + H2O
show the reaction diagram
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-
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r
hexadec-(9Z)-enoyl-[acyl-carrier protein] + reduced flavodoxin + O2
?
show the reaction diagram
hexadecanoyl-[acyl-carrier protein] + reduced flavodoxin + O2
11-hydroxyhexadecanoyl--[acyl-carrier protein] + 12-hydroxyhexadecanoyl-[acyl-carrier protein] + 13-hydroxytetradecanoxl-[acyl-carrier protein] + 14-hydroxytetradecanoxl-[acyl-carrier protein] + 15-hydroxytetradecanoxl-[acyl-carrier protein] + oxidized flavodoxin + H2O
show the reaction diagram
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the enzyme produces mainly the 11- to 15-hydroxy C16 fatty acids
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r
myristoyl-[acyl-carrier protein] + reduced flavodoxin + O2
?
show the reaction diagram
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-
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r
octadec-(9Z)-enoyl-[acyl-carrier protein] + reduced flavodoxin + O2
?
show the reaction diagram
oleoyl-[acyl-carrier protein] + reduced flavodoxin + O2
?
show the reaction diagram
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-
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r
palmitoleoyl-[acyl-carrier protein] + reduced flavodoxin + O2
?
show the reaction diagram
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-
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r
palmitoyl-[acyl-carrier protein] + reduced flavodoxin + O2
?
show the reaction diagram
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-
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r
tetradecanoyl-[acyl-carrier protein] + reduced flavodoxin + O2
11-hydroxytetradecanoyl-[acyl-carrier protein] + 12-hydroxytetradecanoyl-[acyl-carrier protein] + 14-hydroxytetradecanoyl-[acyl-carrier protein] + oxidized flavodoxin + H2O
show the reaction diagram
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-
the enzyme produces mainly the 11-, 12-, and 13-hydroxy C14 fatty acids
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r
tetradecanoyl-[acyl-carrier protein] + reduced flavodoxin + O2
?
show the reaction diagram
tetradecanoyl-[acyl-carrier protein] + reduced flavodoxin + O2
pimeloyl-[acyl carrier protein] + ?
show the reaction diagram
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r
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
a long-chain acyl-[acyl-carrier protein] + reduced flavodoxin + O2
pimeloyl-[acyl-carrier protein] + an n-alkanal + oxidized flavodoxin + H2O
show the reaction diagram
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r
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-bromo-1H-imidazole
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4-phenylimidazole
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econazole
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imidazole
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ketoconazole
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miconazole
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omega-imidazolyl decanoic acid
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omega-imidazolyl lauric acid
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omega-imidazolyl undecanoic acid
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.9
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calculated from amino acid sequence
PDB
SCOP
CATH
ORGANISM
UNIPROT
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44705
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x * 44705, estimated from amino acid sequence
45000
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x * 45000, SDS-PAGE
45348
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x * 45348, electrospray ionization mass spectrometry
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 0.1 M Na HEPES (pH 6.5), 0.15 M Li2SO4, 0.25 M NaCl, 19% (w/v) PEG 4000, and 0.2% (w/v) n-heptyl beta-D-thioglucopyranoside
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE Sephacel column chromatography, hydroxyapatite column chromatography, Q-Sepharose column chromatography, and Sephacryl S-200 gel filtration
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Ni-NTA affinity column chromatography
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Q-Sepharose column chromatography, DEAE-Sepharose column chromatography, hydroxyapatite column chromatography, and Sephacryl S-300 gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli DH5alpha cells
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expressed in Escherichia coli Origami (DE3) cells
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