2.5.1.63: adenosyl-fluoride synthase
This is an abbreviated version!
For detailed information about adenosyl-fluoride synthase, go to the full flat file.
Word Map on EC 2.5.1.63
-
2.5.1.63
-
cattleya
-
fluorometabolite
-
tomography
-
positron
-
fluoroacetate
-
4-fluorothreonine
-
synthesis
-
transhalogenation
-
halide
-
chlorinase
-
tropica
-
organofluorine
-
5'-chloro-5'-deoxyadenosine
-
biotechnology
-
radiosynthesis
-
salinispora
-
desolvation
-
analysis
-
bond-forming
-
halogenase
-
18f-fluoride
-
carbon-fluorine
-
pharmacology
- 2.5.1.63
- cattleya
-
fluorometabolite
-
tomography
-
positron
- fluoroacetate
-
4-fluorothreonine
- synthesis
-
transhalogenation
- halide
- chlorinase
- tropica
-
organofluorine
- 5'-chloro-5'-deoxyadenosine
- biotechnology
-
radiosynthesis
-
salinispora
-
desolvation
- analysis
-
bond-forming
- halogenase
-
18f-fluoride
-
carbon-fluorine
- pharmacology
Reaction
Synonyms
5'-deoxy-5'-fluoroadenosine synthase, 5'-FDA synthase, 5'-FDAS, 5'-fluoro-5'-deoxy adenosine synthetase, 5'-fluoro-5'-deoxyadenosine synthase, 5’-fluorodeoxyadenosine synthase, adenosyl-fluoride synthase, FDAS, flA, flA protein, FlA1, FlA4, fluorinase, fluorinase enzyme, fluorinase, S-adenosyl-L-methionine, fluorination enzyme, NobA, SAM fluorinase, SAMN04487820_1174
ECTree
2.5.1.63 adenosyl-fluoride synthaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 2.5.1.63 - adenosyl-fluoride synthase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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-selenomethionine
S-adenosyl-L-selenomethionine + chloride
use of L-selenomethionine increases the yield by around 2fold
-
-
r
5'-deoxy-5'-fluoroadenosine + L-selenomethionine
Se-adenosyl-L-selenomethionine + fluoride
-
-
-
r
5-deoxy-5'-bromoadenosine + fluoride
5-deoxy-5'-fluoroadenosine + bromide
-
-
-
r
5-deoxy-5'-chloroadenosine + L-methionine
S-adenosyl-L-methionine + chloride
-
-
-
r
5-deoxy-5'-iodoadenosine + fluoride
5-deoxy-5'-fluoroadenosine + iodide
-
-
-
r
S-(2-amino-6-deaminoadenosyl)-L-methionine + fluoride
2-amino-5-deamino-5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-(2-aminoadenosyl)-L-methionine + fluoride
2-amino-5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-(2-chloroadenosyl)-L-methionine + fluoride
2-chloro-5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-(2-ethynyladenosyl)-L-methionine + fluoride
2-ethynyl-5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
2'-deoxyadenosyl-L-methionine + fluoride
2'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
r
2'-deoxyadenosyl-L-methionine + fluoride
2'-deoxy-5'-fluoroadenosine + L-methionine
-
-
in the reverse reaction the enzyme shows 10% activity with the 2'-deoxy compound compared to the activity with the 5'-derivative
-
r
2'-deoxyadenosyl-L-methionine + fluoride
2'-deoxy-5'-fluoroadenosine + L-methionine
-
C-F bond formation, substrate binding structure, NMR and mass spectrometry, overview
in the reverse reaction the enzyme shows 10% activity with the 2'-deoxy compound compared to the activity with the 5'-derivative
-
r
2'-deoxyadenosyl-L-methionine + fluoride
2'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
methylaza-S-adenosyl-L-methionine + fluoride
?
optimal molar ratio of substrate to enzyme in this reaction equals to 112:1 for methylaza-S-adenosyl-L-methionine, modelling of methylaza-S-adenosyl-L-methionine bound in the active site using crystal structure with PDB ID 2V7U, reaction kinetics
-
-
?
methylaza-S-adenosyl-L-methionine + fluoride
?
optimal molar ratio of substrate to enzyme in this reaction equals to 112:1 for methylaza-S-adenosyl-L-methionine, modelling of methylaza-S-adenosyl-L-methionine bound in the active site using crystal structure with PDB ID 2V7U, reaction kinetics
-
-
?
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 + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
-
r
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
r
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
involved in production of toxic fluoroacetate
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
highly specific for S-adenosyl-L-methionine, which is tightly bound to the enzyme at the interface between C-terminal domain of one monomer and the N-terminal domain of the neighbouring monomer
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
reaction mechanism analysis utilizing a stereospecifically labelled substrate (5'R)-[5'-2H]-ATP in a coupled assay, inversion of configuration consistent with a SN2 reaction mechanism
i.e. 5'-FDA, NMR product analysis
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
first committed enzymatic step on the biosynthetic pathway to the fluorometabolites fluoroacetate and 4-fluorothreonine
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
C-F bond formation, substrate binding structure, NMR and mass spectrometry, overview
-
-
r
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
C-F bond formation, the enzyme catalyses an SN2 type reaction mechanism
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
18F-tagged substrate with 3 L-amino acid oxidase to remove the byproduct L-methionine enhancing the production reaction, 37°C, 100 mM Tris-HCl buffer, pH 7.5, up to 4 hours, to produce 18F-tagged product, other enzymes can be added to produce several types of nucleosides
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
20 mg water-absorbing polymer in ionic liquid or 50 mM Tris-HCl buffer, pH 8.0, 50 nM S-adenosyl-L-methionine, 4 mircoM KF, 37°C, exteraction of product 5'-deoxy-5'-fluoroadenosine with diethyl ether
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
optimal molar ratio of substrate to enzyme in this reaction equals to 19:1 for S-adenosyl-L-methionine
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
optimal molar ratio of substrate to enzyme in this reaction equals to 19:1 for S-adenosyl-L-methionine
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
r
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
S-adenosyl-L-methionine + fluoride
5'-deoxy-5'-fluoroadenosine + L-methionine
-
-
-
?
additional information
?
-
-
fluoroacetate and 4-fluorothreonine accumulate in the fermentation media of Streptomyces cattleya at the mM level, when a fluoride source is added to the growth medium
-
-
?
additional information
?
-
-
fluorinase coupled enzyme systems for the synthesis of various 18F-labelled compounds, overview
-
-
?
additional information
?
-
-
substrate specificity, the enzyme does not require a planar ribose conformation of the substrate to catalyse C-F bond formation, overview, the enzyme catalyzes also transhalogenation from 2'-deoxy-5'-chloroadenosine to 2'-deoxy-fluoroadenosine via 2'-deoxy-SeAM, overview
-
-
?
additional information
?
-
the enzyme binds 5',5'-dideoxy-5'-fluoroadenosine with similar affinity as 5'-deoxy-5'-fluoroadenosine, but does not show formation of Se-adenosyl-L-selenomethionine with added L-selenomethionine as it does with 5'-deoxy-5'-fluoroadenosine. The difluoromethyl group bridges interactions that are essential for activation of the single fluorine in 5'-deoxy-5'-fluoroadenosine. An unusual hydrogen bonding interaction between the hydrogen of the difluoromethyl group and one of the hydroxyl oxygens of the tartrate ligand is also observed. The bridging interactions, coupled with the inherently stronger C-F bond in the difluoromethyl group, offers an explanation for why no reaction is observed
-
-
?
additional information
?
-
the enzyme has a specificity tolerance at the 2-position of the adenine base, replacement of hydrogen with an acetylene group at this position gives the modified substrate 5'-chlorodeoxy-2-ethynyladenosine which is an efficient substrate for transhalogenation in the presence of Se-adenosyl-L-selenomethionine. The fluorinase catalyzes a reversible transhalogenation of 5'-chlorodeoxy-2-ethynyladenosine to 5'-fluorodeoxy-2-ethynyladenosine and vice versa using L-selenomethionine and Cl- or F-, respectively. The enzyme is also active in transhalogenation with 5'-chlorodeoxy-2-ethynyladenosine linked to RGD peptides via a PEG linker, overview. The tolerance of the fluorinase to large multimeric peptides suggests that the C-2 position of a chlorinated nucleoside represents a site for the attachment of a diverse range of peptide cargos for use in enzymatic fluorination
-
-
?
additional information
?
-
the fluorinase catalyzes a transhalogenation of 5'-chlorodeoxy-2-ethynyladenosine to 5'-fluorodeoxy-2-ethynyladenosine, substrate specificity, the enzyme does have a specificity weakness at the C-2 position of adenine, overview
-
-
?
additional information
?
-
the fluorinase catalyzes a transhalogenation of 5'-chlorodeoxy-2-ethynyladenosine to 5'-fluorodeoxy-2-ethynyladenosinesubstrate specificity. A two-step radiolabelling protocol of a cancer relevant cRGD peptide is described where the fluorinase enzyme is used to catalyse a transhalogenation reaction to generate [18F]-5'-fluoro-5'-deoxy-2-ethynyladenosine, followed by a radiolabelling reaction with an azide tethered cRGD peptide
-
-
?
additional information
?
-
by coupling the reactions, conversion of 5'-deoxy-5'-chloroadenosine to 5'-fluoro-5'-deoxyadenosine can be achieved
-
-
-
