Information on EC 2.5.1.94 - adenosyl-chloride synthase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.5.1.94
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RECOMMENDED NAME
GeneOntology No.
adenosyl-chloride synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + chloride = 5-deoxy-5-chloroadenosine + L-methionine
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SN2 substitution
-
-
substitution
SN2 nucleophilic substitution
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
salinosporamide A biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:chloride adenosyltransferase
This enzyme, isolated from the marine bacterium Salinispora tropica, catalyses an early step in the pathway leading to biosynthesis of the proteosome inhibitor salinosporamide A. The enzyme is very similar to EC 2.5.1.63, adenosyl-fluoride synthase, but does not accept fluoride.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene aclH
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-
Manually annotated by BRENDA team
Salinospora tropica
a marine organism, gene salL
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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a chlorinase knockout mutated strain of Salinispora tropica is able to biosynthesis the fluorinated analogue of salinosporamide A, when the medium was supplemented with 5-deoxy-5’-fluoroadenosine
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
show the reaction diagram
-
-
-
r
S-adenosyl-L-methionine + bromide
5'-deoxy-5'-bromoadenosine + L-methionine
show the reaction diagram
the enzyme also accepts bromide as substrate (with 90% relative activity compared to chloride) but the brominase activity is probably not biologically relevant in this marine bacterium
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-
r
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
show the reaction diagram
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
show the reaction diagram
-
-
-
-
r
S-adenosyl-L-methionine + iodide
5'-deoxy-5'-iodoadenosine + L-methionine
show the reaction diagram
the enzyme also accepts iodide as substrate (with 33% relative activity compared to chloride) but the iodinase activity is probably not biologically relevant in this marine bacterium
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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
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
show the reaction diagram
Salinospora tropica
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-
-
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r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flavin
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dependent on
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0002
5'-chloro-5'-deoxyadenosine
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.0046
5'-deoxy-5'-iodoadenosine
in 50 mM phosphate buffer (pH 7.9) at 37°C
150
bromide
in 50 mM phosphate buffer (pH 7.9) at 37°C
45
chloride
in 50 mM phosphate buffer (pH 7.9) at 37°C
260
Iodide
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.001
S-adenosyl-L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.2
5'-chloro-5'-deoxyadenosine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.83
5'-deoxy-5'-iodoadenosine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.013
bromide
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.015
chloride
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.005
Iodide
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.2
L-methionine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.015
S-adenosyl-L-methionine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1000
5'-chloro-5'-deoxyadenosine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
28113
181.1
5'-deoxy-5'-iodoadenosine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
41328
0.0000883
bromide
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
905
0.0003
chloride
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
298
0.0000192
Iodide
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
636
0.077
L-methionine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
88
15
S-adenosyl-L-methionine
Salinispora tropica CNB-440
A4X3Q0
in 50 mM phosphate buffer (pH 7.9) at 37°C
24
PDB
SCOP
CATH
ORGANISM
UNIPROT
Salinispora tropica (strain ATCC BAA-916 / DSM 44818 / CNB-440)
Salinispora tropica (strain ATCC BAA-916 / DSM 44818 / CNB-440)
Salinispora tropica (strain ATCC BAA-916 / DSM 44818 / CNB-440)
Salinispora tropica (strain ATCC BAA-916 / DSM 44818 / CNB-440)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
3 * 30000, in solution as determined by sedimentation velocity studies
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homotrimer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 28% (w/v) PEG 3350, 0.3 M KCl, 2 mM dithiothreitol, 0.1 M MOPSO, pH 7.0
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
gene aclH, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis
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gene salL, the gene is located in the middle of this salinosporamide A cluster
Salinospora tropica
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G131S
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the mutation results in instability and arrested chlorination
Y70T
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the mutation leads to a 1000fold loss of chlorination activity
G131S
the mutation leads to the complete loss of all SalL halogenase activities and the inability to crystallize SalL
W129F
the mutant shows 52% chlorinase activity, 76% brominase activity, and 3% iodidase activity compared to the wild type enzyme
Y70T
the mutation results in a two-orders-of-magnitude reduction of SalL activity, the mutant shows 0.07% chlorinase activity, 0.1% brominase activity, and 0.4% iodidase activity compared to the wild type enzyme
Y70T/G131S
the mutant shows 0.3% chlorinase activity, 0.5% brominase activity, and no iodidase activity compared to the wild type enzyme
additional information