We're sorry, but BRENDA doesn't work properly without JavaScript. Please make sure you have JavaScript enabled in your browser settings.
Information on EC 2.5.1.94 - adenosyl-chloride synthase Word Map on EC 2.5.1.94
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
adenosyl-chloride synthase
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
S-adenosyl-L-methionine + chloride = 5-deoxy-5-chloroadenosine + L-methionine
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
substitution
SN2 nucleophilic substitution
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
salinosporamide A biosynthesis
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
5'-chloro-5'-deoxyadenosine synthase
-
-
-
-
S-adenosyl-L-methionine-dependent chlorinase
-
-
SAM-dependent chlorinase
-
-
chlorinase
-
-
-
-
chlorinase
Salinospora tropica
-
-
SalL
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
gene aclH
-
-
brenda
-
-
-
brenda
-
UniProt
brenda
Salinospora tropica
a marine organism, gene salL
-
-
brenda
-
-
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
malfunction
-
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
-
the enzyme catalyzes chlorination, the last step in the aspirochlorine pathway, modeling of the aspirochlorine biosynthesis involving an unusual Phe to Gly conversion, overview
metabolism
Salinospora tropica
-
the enzyme is responsible for salinosporamide-A biosynthesis
physiological function
SalL functions in an orthogonal manner to biological chlorination reactions to initiate the biosynthesis of a new halogenated polyketide synthase building block
physiological function
-
key role of AclH as a chlorinase in the aspirochlorine biosynthesis. Aspirochlorine, or antibiotic A30641, is an epidithiodiketopiperazine toxin distinctive antifungal properties due to selective inhibition of protein biosynthesis produced from Aspergillus oryzae
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
r
S-adenosyl-L-methionine + bromide
5'-deoxy-5'-bromoadenosine + L-methionine
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
-
-
r
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
-
r
S-adenosyl-L-methionine + iodide
5'-deoxy-5'-iodoadenosine + L-methionine
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
-
-
r
additional information
?
-
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
-
-
-
-
?
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
-
-
-
-
?
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
-
chlorinase catalyzes chloride ion SN2 substitution at the C5' of S-adenosyl-L-methionine to generate 5'-deoxy-5'-chloroadenosine
-
-
?
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
-
-
-
r
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
Salinospora tropica
-
-
-
-
r
additional information
?
-
-
although this enzyme utilises bromide and even iodide it does not fluorinate
-
-
-
additional information
?
-
the enzyme does not accept fluoride and 5-deoxy-5'-fluoroadenosine as substrates
-
-
-
additional information
?
-
Salinospora tropica
-
chlorinase does not accept fluoride ion as a substrate
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
Salinospora tropica
-
-
-
-
r
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.2
5'-chloro-5'-deoxyadenosine
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.83
5'-deoxy-5'-iodoadenosine
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.013
bromide
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.015
chloride
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.005
Iodide
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.2
L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.015
S-adenosyl-L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
1000
5'-chloro-5'-deoxyadenosine
in 50 mM phosphate buffer (pH 7.9) at 37°C
181.1
5'-deoxy-5'-iodoadenosine
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.0000883
bromide
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.0003
chloride
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.0000192
Iodide
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.077
L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
15
S-adenosyl-L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
30000
3 * 30000, in solution as determined by sedimentation velocity studies
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
homotrimer
-
x-ray crystallography
homotrimer
3 * 30000, in solution as determined by sedimentation velocity studies
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
expressed in Escherichia coli BL21(DE3) cells
gene aclH, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis
-
gene salL, the gene is located in the middle of this salinosporamide A cluster
Salinospora tropica
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
G131S
-
the mutation results in instability and arrested chlorination
Y70T
-
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
-
construction of an aclH deletion mutant of Aspergillus oryzae RIB40 strain, that is inactive with 3-chloro-L-tyrosine and 3-chloro-DL-phenylalanine. The DaclH mutant culture accumulates dechloroaspirochlorine. Complementation by ectopic integration of aclH in the DaclH mutant restores aspirochlorine production
additional information
Salinospora tropica
-
gene replacement of gene salL from Salinispora tropica by gene flA, EC 2.5.1.63, encoding fluorinase from Streptomaces cattleya, the recombinant fluorinase is functional in Salinispora tropica
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Deng, H.; McMahon, S.A.; Eustaquio, A.S.; Moore, B.S.; Naismith, J.H.; O'Hagan, D.
Mechanistic insights into water activation in SAM hydroxide adenosyltransferase (duf-62)
Chembiochem
10
2455-2459
2009
Salinispora tropica
brenda
Deng, H.; O'Hagan, D.
The fluorinase, the chlorinase and the duf-62 enzymes
Curr. Opin. Chem. Biol.
12
582-592
2008
Salinispora tropica
brenda
Deng, H.; Cobb, S.L.; McEwan, A.R.; McGlinchey, R.P.; Naismith, J.H.; O’Hagan, D.; Robinson, D.A.; Spencer, J.B.
The fluorinase from Streptomyces cattleya is also a chlorinase
Angew. Chem.
45
759-762
2006
Streptomyces cattleya
brenda
Eustaquio, A.S.; Pojer, F.; Noel, J.P.; Moore, B.S.
Discovery and characterization of a marine bacterial SAM-dependent chlorinase
Nat. Chem. Biol.
4
69-74
2008
Salinispora tropica CNB-440 (A4X3Q0)
brenda
Eustaquio, A.S.; McGlinchey, R.P.; Liu, Y.; Hazzard, C.; Beer, L.L.; Florova, G.; Alhamadsheh, M.M.; Lechner, A.; Kale, A.J.; Kobayashi, Y.; Reynolds, K.A.; Moore, B.S.
Biosynthesis of the salinosporamide A polyketide synthase substrate chloroethylmalonyl-coenzyme A from S-adenosyl-L-methionine
Proc. Natl. Acad. Sci. USA
106
12295-12300
2009
Salinispora tropica
brenda
Chankhamjon, P.; Boettger-Schmidt, D.; Scherlach, K.; Urbansky, B.; Lackner, G.; Kalb, D.; Dahse, H.M.; Hoffmeister, D.; Hertweck, C.
Biosynthesis of the halogenated mycotoxin aspirochlorine in koji mold involves a cryptic amino acid conversion
Angew. Chem. Int. Ed. Engl.
53
13409-13413
2014
Aspergillus oryzae
brenda
O'Hagan, D.; Deng, H.
Enzymatic fluorination and biotechnological developments of the fluorinase
Chem. Rev.
115
634-649
2015
Salinospora tropica
brenda
html completed