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
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2.5.1.63
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cattleya
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fluorometabolite
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tomography
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positron
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fluoroacetate
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4-fluorothreonine
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synthesis
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transhalogenation
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halide
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chlorinase
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tropica
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organofluorine
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5'-chloro-5'-deoxyadenosine
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biotechnology
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radiosynthesis
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salinispora
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desolvation
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analysis
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bond-forming
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halogenase
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18f-fluoride
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carbon-fluorine
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pharmacology
- 2.5.1.63
- cattleya
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fluorometabolite
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tomography
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positron
- fluoroacetate
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4-fluorothreonine
- synthesis
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transhalogenation
- halide
- chlorinase
- tropica
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organofluorine
- 5'-chloro-5'-deoxyadenosine
- biotechnology
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radiosynthesis
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salinispora
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desolvation
- analysis
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bond-forming
- halogenase
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18f-fluoride
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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
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Application on EC 2.5.1.63 - adenosyl-fluoride synthase
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APPLICATION 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
analysis
biotechnology
pharmacology
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 click reaction to an azide tethered cRGD peptide. This protocol offers efficient radiolabelling of a biologically relevant peptide construct in water at pH 7.8, 37°C in 2 hours, which is metabolically stable in rats and retains high affinity for alphavbeta3 integrin
synthesis
analysis
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the enzyme is applied as a catalyst for the efficient incorporation of [18F]-fluoride into [18F]-59-fluoro-59-deoxyadenosine, [18F]-59-fluoro-59-deoxyinosine and [18F]-5-fluoro-5-deoxyribose for positron emission tomography, PET, applications, useful for imaging tumors, monitoring the distribution of drugs and identifying cell and receptor degeneration in the brain
analysis
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the fluorinase enzyme from Streptomyces cattleya is applied as a catalyst for the efficient incorporation of [18F]-fluoride into [18F]-59-fluoro-59-deoxyadenosine, [18F]-59-fluoro-59-deoxyinosine and [18F]-5-fluoro-5-deoxyribose for positron emission tomography, PET, applications, useful for imaging tumors, monitoring the distribution of drugs and identifying cell and receptor degeneration in the brain, coupled enzyme system, overview
biotechnology
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fluorochemical production (18F-labelled organic compounds) for medicinal chemistry research (positron emission tomography), when enzyme acts together with other enzymes in the fluorometabolite production (purine nucleoside phosphorylase, isomerase, aldolase, enzyme generating fluoroacetaldehyde in a retro-aldol reaction, fluoroacetaldehyde dehydrogenase or pyridoxal phosphate-dependent enzyme) to generate fluoroacetaldehyde and 4-fluorothreonine
biotechnology
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production of radiolabelled nucleosides as tracers for cancer cell uptake studies via positron emission tomography
biotechnology
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the rate of the enzymatic fluorination reaction can be enhanced by using ionic liquids and immobilizing the enzyme with a water-absorbing polymer which stabilizes the enzyme, 1-octyl-3-methylimidazolium hexafluorophosphate and 1-hexyl-3-methylimidazolium hexafluorophosphate raise the conversion yield 2.4times or 1.6times compared to Tris-HCl buffer, pH 8.0, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium hexafluorophosphate, and 1-hexyl-3-methylimidazolium hexafluorophosphate increase total conversation yields 2.2times to 4times more in immobilized compared to non-immobilized enzyme
biotechnology
the enzyme is used for [18F]-radiolabelling of bioactive peptides, overview
synthesis
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the enzyme is used in biotransformation reaction for production of fluorinated compounds, biotransformation protocols for coupled reaction systems, overview
synthesis
induced production of fluorosalinosporamide by replacing the chlorinase gene salL from Salinispora tropica with the fluorinase gene flA. Maximum yields of 4 mg/l fluorosalinosporamide production are detected at pH 6.0. The fluorosalinosporamide production yields are comparable to those attained through mutasynthesis. The major fluorinated component in the Salinispora tropica salL- flA+ extract is fluorosalinosporamide
synthesis
one-pot three-step continuous enzymatic synthesis of 5-fluoro-5-deoxy-D-ribose from ATP and L-methionine using S-adenosyl-L-methionine synthase, fluorinase and methylthioadenosine nucleosidase in the presence of fluoride ions. The conversion yield is 22.6% of 5-fluoro-5-deoxy-D-ribose from ATP, while the fluoride ions are generated from BF4 ionic liquids and/or the biodegradation of benzotrifluoride in the synthetic process
synthesis
preparation of sodium [18F]-fluoroacetate by generation of 5'-[18F]-fluoro-5'-deoxyadenosine by a fluorinase catalysed reaction of S-adenosyl-L-methionine with no carrier added [18F]-fluoride and then oxidation to [18F]-fluoroacetate by a Kuhn-Roth oxidative degradation. Na [18F]-fluoroacetate can be synthesized in 96% radiochemical purity
synthesis
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 click reaction to an azide tethered cRGD peptide. This protocol offers efficient radiolabelling of a biologically relevant peptide construct in water at pH 7.8, 37°C in 2 hours, which is metabolically stable in rats and retains high affinity for alphavbeta3 integrin
synthesis
substrate tolerance allows a peptide cargo to be tethered to a 5'-chloro-5'-deoxynucleoside substrate for transhalogenation by the enzyme to a 5'-fluoro-5-deoxynucleoside. The reaction is successfully extended from that previously reported for a monomeric cyclic peptide (cRGD) to cargoes of dendritic scaffolds carrying two and four cyclic peptide motifs. The RGD peptide sequence is known to bind upregulated alphaVbeta3 integrin motifs on the surface of cancer cells and it is demonstrated that the fluorinated products have a higher affinity to alphaVbeta3 integrin than their monomeric counterparts. Tolerance of the fluorinase to these 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
synthesis
the enzyme is applicated in positron emission tomography (PET) as a result of its ability to catalyze C-18F bond formation in the presence of [18F]fluoride as the nucleophile. The enzymatic process has a technical advantage in the PET context because [18F]fluoride is generated in the cyclotron as a dilute solution in [18O]water, and the enzyme can use this form of aqueous fluoride directly. This feature obviates the usual requirement to secure dry [18F]fluoride by ion-exchange chromatography. The enzymatic process therefore offers the possibility to directly radiolabel biomolecules in the aqueous phase
synthesis
deveopment of a coupled chlorinase-fluorinase system for rapid transhalogenation. The chlorinase shares a substrate tolerance with the fluorinase, enabling these two enzymes to cooperatively produce 5'-fluorodeoxy-2-ethynyladenosine (5'-FDEA) in up to 91.6% yield in 1 h
synthesis
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preparation of sodium [18F]-fluoroacetate by generation of 5'-[18F]-fluoro-5'-deoxyadenosine by a fluorinase catalysed reaction of S-adenosyl-L-methionine with no carrier added [18F]-fluoride and then oxidation to [18F]-fluoroacetate by a Kuhn-Roth oxidative degradation. Na [18F]-fluoroacetate can be synthesized in 96% radiochemical purity
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synthesis
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induced production of fluorosalinosporamide by replacing the chlorinase gene salL from Salinispora tropica with the fluorinase gene flA. Maximum yields of 4 mg/l fluorosalinosporamide production are detected at pH 6.0. The fluorosalinosporamide production yields are comparable to those attained through mutasynthesis. The major fluorinated component in the Salinispora tropica salL- flA+ extract is fluorosalinosporamide
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synthesis
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one-pot three-step continuous enzymatic synthesis of 5-fluoro-5-deoxy-D-ribose from ATP and L-methionine using S-adenosyl-L-methionine synthase, fluorinase and methylthioadenosine nucleosidase in the presence of fluoride ions. The conversion yield is 22.6% of 5-fluoro-5-deoxy-D-ribose from ATP, while the fluoride ions are generated from BF4 ionic liquids and/or the biodegradation of benzotrifluoride in the synthetic process
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