Strategies for Biodegradation of Fluorinated Compounds

Moreira, Irina S.; Amorim, Catarina L.; Murphy, Cormac D.; Castro, Paula M. L.

doi:10.1007/978-3-030-02369-0_11

Cited by 6 publications

(4 citation statements)

References 237 publications

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“…Fluorine has emerged as a privileged element in medicinal chemistry as well as in agrochemistry and materials science (O’Hagan and Deng 2015 ). Fluorine substitutions are now considered a standard strategy for modulating the properties of chemical leads, despite that environmental contamination by organofluorines is an issue of major concern due to their persistence to biodegradation (Moreira et al 2018 ). While many chemical methods of selective synthesis of organofluorines have been developed, it is attractive to consider biotransformation approaches to selectively access novel organofluorine chemicals, rather than using challenging chemical methods (Wu et al 2020 ).…”

Section: Discovery Of L -Thr Transaldolases From the Biosynthetic Pathways Of Natural Productsmentioning

confidence: 99%

Peculiarities of promiscuous l-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids

Wang¹,

Deng²

2021

Appl Microbiol Biotechnol

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The introduction of β-hydroxy-α-amino acids (βHAAs) into organic molecules has received considerable attention as these molecules have often found widespread applications in bioorganic chemistry, medicinal chemistry and biomaterial science. Despite innovation of asymmetric synthesis of βHAAs, stereoselective synthesis to control the two chiral centres at Cα and Cβ positions is still challenging, with poor atomic economy and multi protection and deprotection steps. These syntheses are often operated under harsh conditions. Therefore, a biotransformation approach using biocatalysts is needed to selectively introduce these two chiral centres into structurally diverse molecules. Yet, there are few ways that enable one-step synthesis of βHAAs. One is to extend the substrate scope of the existing enzyme inventory. Threonine aldolases have been explored to produce βHAAs. However, the enzymes have poor controlled installation at Cβ position, often resulting in a mixture of diastereoisomers which are difficult to be separated. In this respect, l-threonine transaldolases (LTTAs) offer an excellent potential as the enzymes often provide controlled stereochemistry at Cα and Cβ positions. Another is to mine LTTA homologues and engineer the enzymes using directed evolution with the aim of finding engineered biocatalysts to accept broad substrates with enhanced conversion and stereoselectivity. Here, we review the development of LTTAs that incorporate various aldehyde acceptors to generate structurally diverse βHAAs and highlight areas for future developments. Key points • The general mechanism of the transaldolation reaction catalysed by LTTAs • Recent advances in LTTAs from different biosynthetic pathways • Applications of LTTAs as biocatalysts for production of βHAAs

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Section: Discovery Of L -Thr Transaldolases From the Biosynthetic Pathways Of Natural Productsmentioning

confidence: 99%

Peculiarities of promiscuous l-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids

Wang¹,

Deng²

2021

Appl Microbiol Biotechnol

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“…3 In some cases, their stability stems from the presence in their molecular structure of C−Cl or C−F chemical bonds, stronger and more difficult to break than the ordinary C−H counterparts. 4,5 POP accumulation may have adverse effects on both human health and the environment. 6,7 Hence, some of them have been introduced in the European Union watch list.…”

Section: Introductionmentioning

confidence: 99%

“…These molecules, generally referred to as persistent organic pollutants (POPs), are a wide class of compounds including pharmaceuticals as well as personal care products . In some cases, their stability stems from the presence in their molecular structure of C–Cl or C–F chemical bonds, stronger and more difficult to break than the ordinary C–H counterparts. , POP accumulation may have adverse effects on both human health and the environment. , Hence, some of them have been introduced in the European Union watch list . One of these POPs is diclofenac [2-(2-(2,6-dichlorophenylamino)phenyl)acetic acid, DCF, normally sold as its sodium salt under the brand name Voltaren], a nonsteroidal anti-inflammatory drug widely used in many countries of the world to treat pain and inflammatory diseases.…”

Section: Introductionmentioning

confidence: 99%

Thiazole-Decorated PCN-700 Metal–Organic Frameworks for Diclofenac Luminescence Sensing and Adsorption in Wastewater

Provinciali,

Capodilupo,

Mauri

et al. 2024

ACS EST Water

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The defective sites on the eight-connected [Zr 6 O 4 (OH) 8 (H 2 O) 4 ] 8+ nodes of the metal−organic framework (MOF) PCN-700 are the anchoring points for its postsynthetic decoration with extra linkers via solvent-assisted linker incorporation (SALI). The thiazolo [5,4-d]thiazole-2,5-dicarboxylic acid (H 2 TTz) and the newly prepared 2,2′-(1,4-phenylene)bis(4methylthiazole-5-carboxylic acid) (H 2 TzPhTz Me ) have been inserted into PCN-700 to obtain the mixed-linker MOFs (MIXMOFs)

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“…New approaches should be proposed accordingly, where groundbreaking multidisciplinary solutions might be complementary with the current efforts to limit the environmental impact of PFAS pollution. Bioremediation seems to be an environmentally friendly approach to PFAS removal, requiring less harsh conditions than other remediation techniques [20], and potentially reducing operational costs [21], and it is suitable for both polluted water and soil. Even though some organisms, such as bacteria, fungi, and plants, showed to be able to remove PFAS, it is still not clear the possibility of applying bioremediation for such compounds [22].…”

Section: Introductionmentioning

confidence: 99%

Bioremediation of Per- and Poly-Fluoroalkyl Substances (PFAS) by Synechocystis sp. PCC 6803: A Chassis for a Synthetic Biology Approach

Marchetto

Roverso

Righetti

et al. 2021

Life

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One of the main concerns in industrialized countries is represented by per- and poly-fluoroalkyl substances (PFAS), persistent contaminants hardly to be dealt with by conventional wastewater treatment processes. Phyco-remediation was proposed as a green alternative method to treat wastewater. Synechocystis sp. PCC6803 is a unicellular photosynthetic organism candidate for bioremediation approaches based on synthetic biology, as it is able to survive in a wide range of polluted waters. In this work, we assessed the possibility of applying Synechocystis in PFAS-enriched waters, which was never reported in the previous literature. Respirometry was applied to evaluate short-term toxicity of perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS), which did not affect growth up to 0.5 and 4 mg L−1, respectively. Continuous and batch systems were used to assess the long-term effects, and no toxicity was highlighted for both compounds at quite high concentration (1 mg L−1). A partial removal was observed for PFOS and PFOA, (88% and 37%, with removal rates of about 0.15 and 0.36 mg L−1 d−1, respectively). Measurements in fractionated biomass suggested a role for Synechocystis in the sequestration of PFAS: PFOS is mainly internalized in the cell, while PFOA is somehow transformed by still unknown pathways. A preliminary bioinformatic search gave hints on transporters and enzymes possibly involved in such sequestration/transformation processes, opening the route to metabolic engineering in the perspective application of this cyanobacterium as a new phyco-remediation tool, based on synthetic biology.

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Strategies for Biodegradation of Fluorinated Compounds

Cited by 6 publications

References 237 publications

Peculiarities of promiscuous l-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids

Peculiarities of promiscuous l-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids

Thiazole-Decorated PCN-700 Metal–Organic Frameworks for Diclofenac Luminescence Sensing and Adsorption in Wastewater

Bioremediation of Per- and Poly-Fluoroalkyl Substances (PFAS) by Synechocystis sp. PCC 6803: A Chassis for a Synthetic Biology Approach

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