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
8-amino-7-oxononanoate biosynthesis II
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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
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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
(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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?
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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?
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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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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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)
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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