Polymer-immobilized fluorinase: Recyclable catalyst for fluorination reactions

Sergeev, Maxim; Morgia, Federica; Javed, Muhammad Rashed; Doi, Mami; Keng, Pei Yuin

doi:10.1016/j.molcatb.2013.03.009

Cited by 20 publications

(17 citation statements)

References 29 publications

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“…369 A polymer-supported fluorinase has also been used for these radiofluorinations which, by allowing more facile removal of biocatalyst, may allow more efficient syntheses of these compounds with higher RCY. 371,372 The Combination of the above cascade with a phytase enzyme allows the nucleobase portion of 18 F-FDA to be replaced with a hydroxyl group, affording 5'- 18 F ribose (101). 370,374 101 is of particular interest because of the potential to exploit this primed substrate in bio-conjugation due to its propensity for ring-opening.…”

Section: Discovery Of Fluorinases In Naturementioning

confidence: 99%

Development of Halogenase Enzymes for Use in Synthesis

Latham

Brandenburger

Shepherd³

et al. 2017

Chem. Rev.

285

244

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Nature has evolved halogenase enzymes to regioselectively halogenate a diverse range of biosynthetic precursors, with the halogens introduced often having a profound effect on the biological activity of the resulting natural products. Synthetic endeavours to create non-natural bioactive small molecules for pharmaceutical and agrochemical applications have also arrived at a similar conclusion -halogens can dramatically improve the properties of organic molecules for selective modulation of biological targets in vivo. Consequently a high proportion of pharmaceuticals and agrochemicals on the market today possess halogens. Halogenated organic compounds are also common intermediates in synthesis and are particularly valuable in metal catalyzed cross-coupling reactions.Despite the potential utility of organohalogens, traditional non-enzymatic halogenation chemistry utilizes deleterious reagents and often lacks regiocontrol. Reliable, facile and cleaner methods for the regioselective halogenation of organic compounds are therefore essential in the development of economical and environmentally-friendly industrial processes. A potential avenue towards such methods is the use of halogenase enzymes, responsible for the biosynthesis of halogenated natural products, as biocatalysts. This review will discuss the advances towards this goal thus far, in addition to untapped potential sources of such biocatalysts and how further development of the enzymes may be focused in order to achieve the goal of industrial scale biohalogenation.

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Section: Discovery Of Fluorinases In Naturementioning

confidence: 99%

Development of Halogenase Enzymes for Use in Synthesis

Latham

Brandenburger

Shepherd³

et al. 2017

Chem. Rev.

285

244

View full text Add to dashboard Cite

show abstract

“…[136][137][138] Additionally, in 2013, Sergeev et al successfully immobilised the fluorinase enzyme discovered by O'Hagan (vide supra), 124 onto a poly(GMA-EDMA) monolith. 139 The supported enzyme was shown to be an efficient and reusable catalyst for both fluorination and radiofluorination of the specific substrate, SAM, to 5-FDA and 5-18 FDA. 139 catalytic methods for C(sp 3 )-F formation are still characterised by limited levels of productivity, and/or poor atom economy, with large excesses of expensive fluorinating reagents and/or fluorine salts typically required.…”

Section: Fluorination Reactions Catalysed By Heterogeneous Catalystsmentioning

confidence: 99%

“…139 The supported enzyme was shown to be an efficient and reusable catalyst for both fluorination and radiofluorination of the specific substrate, SAM, to 5-FDA and 5-18 FDA. 139 catalytic methods for C(sp 3 )-F formation are still characterised by limited levels of productivity, and/or poor atom economy, with large excesses of expensive fluorinating reagents and/or fluorine salts typically required. As such, future studies should address the development of catalytic fluorination methods able to achieve C(sp 3 )-F synthesis in a more sustainable and efficient manner.…”

Section: Fluorination Reactions Catalysed By Heterogeneous Catalystsmentioning

confidence: 99%

Catalytic C(sp³)–F bond formation: recent achievements and pertaining challenges

Tarantino

Hammond

2020

Green Chem.

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“…There are numerous studies in the literature illustrating the application of fluorinase in this field. [35,[148][149][150][151][152][153][154][155][156] The fluorinase enzyme can also be employed as a valuable tool to enlarge the diversity of fluorometabolite structures through genetic engineering synthesis. The study conducted by Eust aquio et al [37] in which the production of fluorosalinosporamide (Figure 4(B), compound 5) was achieved by replacing the chlorinase gene with the fluorinase gene in S. tropica, constitutes a good example of this.…”

Section: '-Fda Phosphorylasementioning

confidence: 99%

Natural production of fluorinated compounds and biotechnological prospects of the fluorinase enzyme

Carvalho

Oliveira

2017

Critical Reviews in Biotechnology

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Fluorinated compounds are finding increasing uses in several applications. They are employed in almost all areas of modern society. These compounds are all produced by chemical synthesis and their abundance highly contrasts with fluorinated molecules of natural origin. To date, only some plants and a handful of actinomycetes species are known to produce a small number of fluorinated compounds that include fluoroacetate (FA), some ω-fluorinated fatty acids, nucleocidin, 4-fluorothreonine (4-FT), and the more recently identified (2R3S4S)-5-fluoro-2,3,4-trihydroxypentanoic acid. This largely differs from other naturally produced halogenated compounds, which totals more than 5000. The mechanisms underlying biological fluorination have been uncovered after discovering the first actinomycete species, Streptomyces cattleya, that is capable of producing FA and 4-FT, and a fluorinase has been identified as the enzyme responsible for the formation of the C-F bond. The discovery of this enzyme has opened new perspectives for the biotechnological production of fluorinated compounds and many advancements have been achieved in its application mainly as a biocatalyst for the synthesis of [F]-labeled radiotracers for medical imaging. Natural fluorinated compounds may also be derived from abiogenic sources, such as volcanoes and rocks, though their concentrations and production mechanisms are not well known. This review provides an outlook of what is currently known about fluorinated compounds with natural origin. The paucity of these compounds and the biological mechanisms responsible for their production are addressed. Due to its relevance, special emphasis is given to the discovery, characterization and biotechnological potential of the unique fluorinase enzyme.

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Polymer-immobilized fluorinase: Recyclable catalyst for fluorination reactions

Cited by 20 publications

References 29 publications

Development of Halogenase Enzymes for Use in Synthesis

Development of Halogenase Enzymes for Use in Synthesis

Catalytic C(sp³)–F bond formation: recent achievements and pertaining challenges

Natural production of fluorinated compounds and biotechnological prospects of the fluorinase enzyme

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Polymer-immobilized fluorinase: Recyclable catalyst for fluorination reactions

Cited by 20 publications

References 29 publications

Development of Halogenase Enzymes for Use in Synthesis

Development of Halogenase Enzymes for Use in Synthesis

Catalytic C(sp3)–F bond formation: recent achievements and pertaining challenges

Natural production of fluorinated compounds and biotechnological prospects of the fluorinase enzyme

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Product

Resources

About

Catalytic C(sp³)–F bond formation: recent achievements and pertaining challenges