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Information on EC 2.5.1.94 - adenosyl-chloride synthase and Organism(s) Salinispora tropica and UniProt Accession A4X3Q0

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EC Tree
IUBMB Comments
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.
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This record set is specific for:
Salinispora tropica
UNIPROT: A4X3Q0
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The taxonomic range for the selected organisms is: Salinispora tropica
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
chlorinase, sam-dependent chlorinase, s-adenosyl-l-methionine-dependent chlorinase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5'-chloro-5'-deoxyadenosine synthase
-
-
-
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chlorinase
S-adenosyl-L-methionine-dependent chlorinase
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-
SAM-dependent chlorinase
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-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SN2 substitution
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-
PATHWAY SOURCE
PATHWAYS
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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.
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
5-deoxy-5-chloroadenosine + S-(2-amino-2-carboxylethyl)-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-(2-amino-2-oxoethyl)-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-allyl-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-benzyl-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-butyl-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-ethyl-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-phenylethyl-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-propargyl-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
5-deoxy-5-chloroadenosine + S-propyl-L-homocysteine
?
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
show the reaction diagram
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + L-methionine
show the reaction diagram
-
-
-
-
r
additional information
?
-
NATURAL SUBSTRATE
NATURAL 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 + chloride
5'-deoxy-5'-chloroadenosine + L-methionine
show the reaction diagram
-
-
-
-
r
S-adenosyl-L-methionine + chloride
5-deoxy-5-chloroadenosine + L-methionine
show the reaction diagram
-
-
-
-
r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
-
-
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
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the enzyme is responsible for salinosporamide-A biosynthesis
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homotrimer
-
x-ray crystallography
PROTEIN VARIANTS
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
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
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni2+-NTA resin column chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
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gene salL, the gene is located in the middle of this salinosporamide A cluster
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Manually annotated by BRENDA team
Deng, H.; O'Hagan, D.
The fluorinase, the chlorinase and the duf-62 enzymes
Curr. Opin. Chem. Biol.
12
582-592
2008
Salinispora tropica
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
O'Hagan, D.; Deng, H.
Enzymatic fluorination and biotechnological developments of the fluorinase
Chem. Rev.
115
634-649
2015
Salinispora tropica
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team