Information on EC 3.1.1.85 - pimelyl-[acyl-carrier protein] methyl ester esterase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Proteobacteria

EC NUMBER
COMMENTARY
3.1.1.85
-
RECOMMENDED NAME
GeneOntology No.
pimelyl-[acyl-carrier protein] methyl ester esterase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
pimeloyl-[acyl-carrier protein] methyl ester + H2O = pimeloyl-[acyl-carrier protein] + methanol
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
8-amino-7-oxononanoate biosynthesis I
-
-
Biotin metabolism
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
pimelyl-[acyl-carrier protein] methyl ester hydrolase
Involved in biotin biosynthesis in Gram-negative bacteria. The enzyme exhibits carboxylesterase activity, particularly toward substrates with short acyl chains [1,2]. Even though the enzyme can interact with coenzyme A thioesters [3], the in vivo role of the enzyme is to hydrolyse the methyl ester of pimeloyl-[acyl carrier protein], terminating the part of the biotin biosynthesis pathway that is catalysed by the fatty acid elongation enzymes [4].
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
BioH
-
-
-
-
BioH
Escherichia coli JM101
-
-
-
BioH
Serratia marcescens 8000
-
-
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Escherichia coli DH5-alpha
-
SwissProt
Manually annotated by BRENDA team
Escherichia coli JM101
-
-
-
Manually annotated by BRENDA team
Serratia marcescens 8000
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
BioH is involved in biotin biosynthesis
metabolism
-
the bioH gene product is required for the synthesis of pimeloyl-CoA
metabolism
-
BioH is involved in the early step of biotin synthesis
metabolism
Escherichia coli JM101, Neisseria meningitidis H44/76
-
the bioH gene product is required for the synthesis of pimeloyl-CoA
-
metabolism
Serratia marcescens 8000
-
BioH is involved in the early step of biotin synthesis
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-nitrophenyl acetate + H2O
?
show the reaction diagram
highest carboxylesterase activity
-
-
?
4-nitrophenyl butyrate + H2O
?
show the reaction diagram
-
-
-
?
4-nitrophenyl caprate + H2O
?
show the reaction diagram
-
-
-
?
4-nitrophenyl caproate + H2O
?
show the reaction diagram
-
-
-
?
4-nitrophenyl laurate + H2O
?
show the reaction diagram
-
-
-
?
4-nitrophenyl palmitate + H2O
?
show the reaction diagram
-
-
-
?
4-nitrophenyl propionate + H2O
?
show the reaction diagram
-
-
-
?
4-nitrophenyl stearate + H2O
?
show the reaction diagram
very low carboxylesterase activity
-
-
?
adipyl-[acyl-carrier protein] methyl ester + H2O
adipyl-[acyl-carrier nprotein] + methanol
show the reaction diagram
-
-
-
?
pimeloyl-[acyl-carrier protein] butyl ester + H2O
pimeloyl-[acyl-carrier protein] + butanol
show the reaction diagram
-
-
-
?
pimeloyl-[acyl-carrier protein] ethyl ester + H2O
pimeloyl-[acyl-carrier protein] + ethanol
show the reaction diagram
-
-
-
?
pimeloyl-[acyl-carrier protein] methyl ester + H2O
pimeloyl-[acyl-carrier protein] + methanol
show the reaction diagram
-
-
-
?
pimeloyl-[acyl-carrier protein] propyl ester + H2O
pimeloyl-[acyl-carrier protein] + propanol
show the reaction diagram
-
-
-
?
pimelyl-[acyl-carrier protein] methyl ester + H2O
pimelyl-[acyl-carrier protein] + methanol
show the reaction diagram
-
-
?
suberyl-[acyl-carrier protein] methyl ester + H2O
suberyl-[acyl-carrier protein] + methanol
show the reaction diagram
-
-
-
?
azelayl-[acyl-carrier protein] methyl ester + H2O
azelayl-[acyl-carrier protein] + methanol
show the reaction diagram
-
-
-
?
additional information
?
-
-
BioH fails to cleave malonyl-[acyl-carrier protein] methyl ester and succinyl-[acyl-carrier protein] methyl ester
-
-
-
additional information
?
-
purified BioH shows low enzymatic activities for thioesterase (using palmitoyl-CoA as a substrate), lipase (using olive oil as a substrate), and aminopeptidase (using leucine-4-anilide as a substrate) and shows no detectable enzymatic activity for phosphatase (using 4-nitrophenyl phosphate as a substrate), trypsin-like endopeptidase (using benzoyl-arginine-4-nitroanilide as a substrate), or bromoperoxidase (phenol red and monochlorodimedone as potential substrates)
-
-
-
additional information
?
-
Serratia marcescens, Serratia marcescens 8000
-
the bioH gene product from Serratia marcescens shows esterase activity, which may imply the hydrolysis of a precursor leading to pimeloyl-CoA ester
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
phenylmethylsulfonyl fluoride
10.5% residual activity after 10 min of incubation with 2 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.29
4-nitrophenyl acetate
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
0.33
4-nitrophenyl butyrate
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
0.25
4-nitrophenyl caproate
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
0.6
4-nitrophenyl laurate
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
0.35
4-nitrophenyl propionate
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
18.5
4-nitrophenyl acetate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
6.1
4-nitrophenyl butyrate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
4
4-nitrophenyl caproate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
1.5
4-nitrophenyl laurate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
13.1
4-nitrophenyl propionate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
63.8
4-nitrophenyl acetate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
418
18.5
4-nitrophenyl butyrate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
522
16
4-nitrophenyl caproate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
2790
2.5
4-nitrophenyl laurate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
2511
37.4
4-nitrophenyl propionate
Escherichia coli
P13001
in 50 mM HEPES-K (pH 7.5) buffer, at 37C
1942
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Serratia marcescens 8000
-
-
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
27040
-
calculated from amino acid sequence
715005
28000
-
SDS-PAGE
715005
28000
-
SDS-PAGE
715104
28510
-
calculated from amino acid sequence
715005
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 1.2 M sodium citrate trihydrate and 0.1 M Tris-HCl (pH 8.0), at 21C
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA column chromatography
Q-Sepharose column chromatography and gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli Hms174(DE3) cells
-
expressed in the Escherichia coli auxotroph strain B834 (DE3)
expressed in Escherichia coli Hms174(DE3) cells
-
expressed in Escherichia coli K-12 DH5 cells
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
S53A
-
the mutant is insoluble
S82A
-
inactive
S82A
-
the mutation does not prevent coenzyme A binding
S53A
Escherichia coli JM101
-
the mutant is insoluble
-
S82A
Escherichia coli JM101
-
the mutation does not prevent coenzyme A binding
-