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2'-deoxy-2-ethynyladenosyl-L-methionine + fluoride
2'-deoxy-2-ethynyl-5'-fluoroadenosine + L-methionine
2'-deoxyadenosyl-L-methionine + fluoride
2'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
r
5-deoxy-5'-bromoadenosine + fluoride
5-deoxy-5'-fluoroadenosine + bromide
-
-
-
r
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
5-deoxy-5'-iodoadenosine + fluoride
5-deoxy-5'-fluoroadenosine + iodide
-
-
-
r
5-deoxy-5-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + S-(2-amino-2-carboxylethyl)-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-(2-amino-2-oxoethyl)-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-allyl-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-benzyl-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-butyl-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-ethyl-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-phenylethyl-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-propargyl-L-homocysteine
?
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-propyl-L-homocysteine
?
-
-
-
-
?
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 + chloride
5-deoxy-5'-chloroadenosine + L-methionine
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
?
-
2'-deoxy-2-ethynyladenosyl-L-methionine + fluoride
2'-deoxy-2-ethynyl-5'-fluoroadenosine + L-methionine
-
-
-
-
r
2'-deoxy-2-ethynyladenosyl-L-methionine + fluoride
2'-deoxy-2-ethynyl-5'-fluoroadenosine + L-methionine
-
-
-
-
r
2'-deoxy-2-ethynyladenosyl-L-methionine + fluoride
2'-deoxy-2-ethynyl-5'-fluoroadenosine + L-methionine
-
-
-
-
r
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
r
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
-
r
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
r
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
-
r
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
-
r
5-deoxy-5-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
-
r
5-deoxy-5-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
most efficient reaction
-
-
r
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
-
-
-
-
?
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
-
-
-
-
r
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
-
-
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5'-chloroadenosine + L-methionine
-
-
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5'-chloroadenosine + L-methionine
-
-
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + L-methionine
-
-
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + L-methionine
-
-
-
-
r
additional information
?
-
-
although this enzyme utilises bromide and even iodide it does not fluorinate
-
-
?
additional information
?
-
-
chlorinase does not accept fluoride ion as a substrate
-
-
?
additional information
?
-
the enzyme does not accept fluoride and 5-deoxy-5'-fluoroadenosine as substrates
-
-
?
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5-deoxy-5-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
-
-
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + L-methionine
5-deoxy-5-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
-
r
5-deoxy-5-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
most efficient reaction
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + L-methionine
-
-
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + L-methionine
-
-
-
-
r
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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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
0.0097
5-deoxy-5'-bromoadenosine
37°C, direct displacement reaction in the absence of L-methionine or S-adenosyl-L-methionine, pH not specified in the publication
0.0095 - 0.014
5-deoxy-5'-chloroadenosine
0.00945 - 0.01398
5-deoxy-5-chloroadenosine
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 - 0.0157
S-adenosyl-L-methionine
0.0095
5-deoxy-5'-chloroadenosine
-
pH not specified in the publication, temperature not specified in the publication
0.014
5-deoxy-5'-chloroadenosine
-
pH not specified in the publication, temperature not specified in the publication
0.00945
5-deoxy-5-chloroadenosine
-
isoform ClA2, at pH 7.8 and 37°C
0.01398
5-deoxy-5-chloroadenosine
-
isoform ClA1, at pH 7.8 and 37°C
0.001
S-adenosyl-L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.00248
S-adenosyl-L-methionine
-
isoform ClA2, at pH 7.8 and 37°C
0.0025
S-adenosyl-L-methionine
-
pH not specified in the publication, temperature not specified in the publication
0.01569
S-adenosyl-L-methionine
-
isoform ClA1, at pH 7.8 and 37°C
0.0157
S-adenosyl-L-methionine
-
pH not specified in the publication, temperature not specified in the publication
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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
0.0003
5-deoxy-5'-bromoadenosine
37°C, direct displacement reaction in the absence of L-methionine or S-adenosyl-L-methionine, pH not specified in the publication
0.208 - 0.248
5-deoxy-5'-chloroadenosine
0.208 - 0.249
5-deoxy-5-chloroadenosine
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
0.011 - 0.078
S-adenosyl-L-methionine
0.208
5-deoxy-5'-chloroadenosine
-
pH not specified in the publication, temperature not specified in the publication
0.248
5-deoxy-5'-chloroadenosine
-
pH not specified in the publication, temperature not specified in the publication
0.208
5-deoxy-5-chloroadenosine
-
isoform ClA1, at pH 7.8 and 37°C
0.249
5-deoxy-5-chloroadenosine
-
isoform ClA2, at pH 7.8 and 37°C
0.011
S-adenosyl-L-methionine
-
pH not specified in the publication, temperature not specified in the publication
0.011
S-adenosyl-L-methionine
-
isoform ClA2, at pH 7.8 and 37°C
0.015
S-adenosyl-L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
0.078
S-adenosyl-L-methionine
-
pH not specified in the publication, temperature not specified in the publication
0.078
S-adenosyl-L-methionine
-
isoform ClA1, at pH 7.8 and 37°C
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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
0.035
5-deoxy-5'-bromoadenosine
37°C, direct displacement reaction in the absence of L-methionine or S-adenosyl-L-methionine, pH not specified in the publication
14.89 - 26.29
5-deoxy-5'-chloroadenosine
14.89 - 26.29
5-deoxy-5-chloroadenosine
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
4.5 - 15
S-adenosyl-L-methionine
14.89
5-deoxy-5'-chloroadenosine
-
pH not specified in the publication, temperature not specified in the publication
26.29
5-deoxy-5'-chloroadenosine
-
pH not specified in the publication, temperature not specified in the publication
14.89
5-deoxy-5-chloroadenosine
-
isoform ClA1, at pH 7.8 and 37°C
26.29
5-deoxy-5-chloroadenosine
-
isoform ClA2, at pH 7.8 and 37°C
4.5
S-adenosyl-L-methionine
-
isoform ClA2, at pH 7.8 and 37°C
4.502
S-adenosyl-L-methionine
-
pH not specified in the publication, temperature not specified in the publication
4.968
S-adenosyl-L-methionine
-
pH not specified in the publication, temperature not specified in the publication
4.97
S-adenosyl-L-methionine
-
isoform ClA1, at pH 7.8 and 37°C
15
S-adenosyl-L-methionine
in 50 mM phosphate buffer (pH 7.9) at 37°C
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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
-
the enzyme is responsible for salinosporamide-A biosynthesis
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
-
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
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
-
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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
-
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
-
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
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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.; OHagan, 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, Aspergillus oryzae RIB 40
brenda
O'Hagan, D.; Deng, H.
Enzymatic fluorination and biotechnological developments of the fluorinase
Chem. Rev.
115
634-649
2015
Salinispora tropica
brenda
Sun, H.; Zhao, H.; Ang, E.
A coupled chlorinase-fluorinase system with a high efficiency of trans-halogenation and a shared substrate tolerance
Chem. Commun. (Camb.)
54
9458-9461
2018
uncultured bacterium, Streptomyces albulus, Umezawaea tangerina, Umezawaea tangerina NRRL B-24463
brenda
Thapa, H.R.; Lail, A.J.; Garg, N.; Agarwal, V.
Chemoenzymatic synthesis of starting materials and characterization of halogenases requiring acyl carrier protein-tethered substrates
Methods Enzymol.
604
333-366
2018
Salinispora tropica
brenda
Lowe, P.T.; Cobb, S.L.; OHagan, D.
An enzymatic Finkelstein reaction fluorinase catalyses direct halogen exchange
Org. Biomol. Chem.
17
7493-7496
2019
Streptomyces cattleya (Q70GK9)
brenda