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Accessing active fragments for drug discovery utilising nitroreductase biocatalysis. (2024)
Journal Article
Holder, L., Yuce, E., Oriomah, G., Jenkins, A.-P., Reynisson, J., Winter, A., & Cosgrove, S. (in press). Accessing active fragments for drug discovery utilising nitroreductase biocatalysis. ChemBioChem, Article e202400428. https://doi.org/10.1002/cbic.202400428

Biocatalysis has played a limited role in the early stages of drug discovery. This is often attributed to the limited substrate scope of enzymes not affording access to vast areas of novel chemical space. Here, we have shown a promiscuous nitroreduct... Read More about Accessing active fragments for drug discovery utilising nitroreductase biocatalysis..

Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides (2023)
Journal Article
Wahart, A. J. C., Dolan, J. P., Anderson, S. D., Cheallaigh, A. N., Staniland, J., Lima, M. A., …Cosgrove, S. C. (2023). Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides. ChemBioChem, Article e202300752. https://doi.org/10.1002/cbic.202300752

Wahart et al. demonstrate the use of an immobilised oxidase enzyme coupled to an extractive amino resin for the bioremediation of a common industrial surfactant. This allows the facile purification of alkyl monoglucosides without the need for high en... Read More about Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides.

Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides. (2023)
Journal Article
Wahart, A. J. C., Dolan, J. P., Anderson, S. D., Cheallaigh, A. N., Staniland, J., Lima, M. A., …Cosgrove, S. C. (in press). Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides. ChemBioChem, Article e202300625. https://doi.org/10.1002/cbic.202300625

As the world moves towards net-zero carbon emissions, the development of sustainable chemical manufacturing processes is essential. Within manufacturing, purification by distillation is often used, however this process is energy intensive and methods... Read More about Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides..

RetroBioCat Database: A Platform for Collaborative Curation and Automated Meta-Analysis of Biocatalysis Data (2023)
Journal Article
Finnigan, W., Lubberink, M., Hepworth, L. J., Citoler, J., Mattey, A. P., Ford, G. J., …Turner, N. J. (2023). RetroBioCat Database: A Platform for Collaborative Curation and Automated Meta-Analysis of Biocatalysis Data. ACS catalysis, 13(17), 11771-11780. https://doi.org/10.1021/acscatal.3c01418

Despite the increasing use of biocatalysis for organic synthesis, there are currently no databases that adequately capture synthetic biotransformations. The lack of a biocatalysis database prevents accelerating biocatalyst characterization efforts fr... Read More about RetroBioCat Database: A Platform for Collaborative Curation and Automated Meta-Analysis of Biocatalysis Data.

Realizing the Continuous Chemoenzymatic Synthesis of Anilines Using an Immobilized Nitroreductase (2023)
Journal Article
Cosgrove, S. C., Miller, G. J., Bornadel, A., & Dominguez, B. (2023). Realizing the Continuous Chemoenzymatic Synthesis of Anilines Using an Immobilized Nitroreductase. ACS sustainable chemistry & engineering, 11(23), 8556-8561. https://doi.org/10.1021/acssuschemeng.3c01204

The use of biocatalysis for classically synthetic transformations has seen an increase in recent years, driven by the sustainability credentials bio-based approaches can offer the chemical industry. Despite this, the biocatalytic reduction of aromati... Read More about Realizing the Continuous Chemoenzymatic Synthesis of Anilines Using an Immobilized Nitroreductase.

One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines (2023)
Journal Article
Sangster, J. J., Ruscoe, R. E., Cosgrove, S. C., Mangas-Sánchez, J., & Turner, N. J. (2023). One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines. Journal of the American Chemical Society, 145(8), 4431-4437. https://doi.org/10.1021/jacs.2c09176

Herein, we report a one-pot, chemoenzymatic process for the synthesis of enantioenriched C(1)-allylated tetrahydroisoquinolines. This transformation couples a monoamine oxidase (MAO-N)-catalyzed oxidation with a metal catalyzed allylboration, followe... Read More about One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines.

Biocatalytic Approaches to Building Blocks for Enzymatic and Chemical Glycan Synthesis (2022)
Journal Article
Cosgrove, Miller, & Dolan. (2022). Biocatalytic Approaches to Building Blocks for Enzymatic and Chemical Glycan Synthesis. JACS Au, 47-61. https://doi.org/10.1021/jacsau.2c00529

While the field of biocatalysis has bloomed over the past 20–30 years, advances in the understanding and improvement of carbohydrate-active enzymes, in particular, the sugar nucleotides involved in glycan building block biosynthesis, have progressed... Read More about Biocatalytic Approaches to Building Blocks for Enzymatic and Chemical Glycan Synthesis.

Advances in biocatalytic and chemoenzymatic synthesis of nucleoside analogues. (2022)
Journal Article
Cosgrove, S. C., & Miller, G. J. (2022). Advances in biocatalytic and chemoenzymatic synthesis of nucleoside analogues. Expert Opinion on Drug Discovery, 17(4), 355-364. https://doi.org/10.1080/17460441.2022.2039620

INTRODUCTION: Nucleoside analogues represent a cornerstone of achievement in drug discovery, rising to prominence particularly in the fields of antiviral and anticancer discovery over the last 60 years. Traditionally accessed using chemical synthesis... Read More about Advances in biocatalytic and chemoenzymatic synthesis of nucleoside analogues..

Oxidase enzymes as sustainable oxidation catalysts (2022)
Journal Article
Wahart, A. J. C., Staniland, J., Miller, G. J., & Cosgrove, S. C. (2022). Oxidase enzymes as sustainable oxidation catalysts. Royal Society Open Science, 9(1), https://doi.org/10.1098/rsos.211572

Oxidation is one of the most important processes used by the chemical industry. However, many of the methods that are used pose significant sustainability and environmental issues. Biocatalytic oxidation offers an alternative to these methods, with a... Read More about Oxidase enzymes as sustainable oxidation catalysts.

Reaching new biocatalytic reactivity using continuous flow reactors (2021)
Journal Article
Cosgrove, S. C., & Mattey, A. P. (2022). Reaching new biocatalytic reactivity using continuous flow reactors. Chemistry - A European Journal, 28(13), https://doi.org/10.1002/chem.202103607

The use of flow reactors in biocatalysis has increased significantly in recent years. Chemists have begun to design flow systems that even allow new biocatalytic reactions to take place. This concept article will focus on the design of flow systems t... Read More about Reaching new biocatalytic reactivity using continuous flow reactors.

Rücktitelbild: Development of Continuous Flow Systems to Access Secondary Amines Through Previously Incompatible Biocatalytic Cascades (Angew. Chem. 34/2021) (2021)
Journal Article
Mattey, A. P., Ford, G. J., Citoler, J., Baldwin, C., Marshall, J. R., Palmer, R. B., …Flitsch, S. L. (2021). Rücktitelbild: Development of Continuous Flow Systems to Access Secondary Amines Through Previously Incompatible Biocatalytic Cascades (Angew. Chem. 34/2021). Angewandte Chemie, 133(34), 19040-19040. https://doi.org/10.1002/ange.202107128

Back Cover: Development of Continuous Flow Systems to Access Secondary Amines Through Previously Incompatible Biocatalytic Cascades (Angew. Chem. Int. Ed. 34/2021) (2021)
Journal Article
Mattey, A. P., Ford, G. J., Citoler, J., Baldwin, C., Marshall, J. R., Palmer, R. B., …Flitsch, S. L. (2021). Back Cover: Development of Continuous Flow Systems to Access Secondary Amines Through Previously Incompatible Biocatalytic Cascades (Angew. Chem. Int. Ed. 34/2021). Angewandte Chemie International Edition, 60(34), 18892-18892. https://doi.org/10.1002/anie.202107128

Development of continuous flow systems to access secondary amines through previously incompatible biocatalytic cascades. (2021)
Journal Article
Mattey, A. P., Ford, G. J., Citoler, J., Baldwin, C., Marshall, J. R., Palmer, R. B., …Flitsch, S. L. (2021). Development of continuous flow systems to access secondary amines through previously incompatible biocatalytic cascades. Angewandte Chemie International Edition, 60(34), 18660-18665. https://doi.org/10.1002/anie.202103805

A key aim of biocatalysis is to mimic the ability of eukaryotic cells to carry out multistep cascades in a controlled and selective way. As biocatalytic cascades get more complex, reactions become unattainable under typical batch conditions. Here a n... Read More about Development of continuous flow systems to access secondary amines through previously incompatible biocatalytic cascades..

Development of Continuous Flow Systems to Access Secondary Amines Through Previously Incompatible Biocatalytic Cascades** (2021)
Journal Article
Cosgrove, S. C., Mattey, A. P., Ford, G. J., Citoler, J., Baldwin, C., Marshall, J. R., …Flitsch, S. L. (2021). Development of Continuous Flow Systems to Access Secondary Amines Through Previously Incompatible Biocatalytic Cascades**. Angewandte Chemie, 133(34), 18808-18813. https://doi.org/10.1002/ange.202103805

A key aim of biocatalysis is to mimic the ability of eukaryotic cells to carry out multistep cascades in a controlled and selective way. As biocatalytic cascades get more complex, reactions become unattainable under typical batch conditions. Here a n... Read More about Development of Continuous Flow Systems to Access Secondary Amines Through Previously Incompatible Biocatalytic Cascades**.

Production of High Value Amine Intermediates via Biocatalytic Cascades in Continuous Flow (2021)
Journal Article
Baldwin, C., Thompson, M., Turner, N., Pamer, R., Ford, G., Citoler, J., …Cosgrove, S. (2021). Production of High Value Amine Intermediates via Biocatalytic Cascades in Continuous Flow. ChemRxiv, https://doi.org/10.26434/chemrxiv.14039141.v1

A key aim of biocatalysis is to mimic the ability of eukaryotic cells to carry out compartmentalized multistep cascades in a controlled and selective way. As biocatalytic cascades get longer and more complex, reactions become unattainable under typic... Read More about Production of High Value Amine Intermediates via Biocatalytic Cascades in Continuous Flow.

Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases (2020)
Journal Article
Mangas-Sanchez, J., Sharma, M., Cosgrove, S. C., Ramsden, J. I., Marshall, J. R., Thorpe, T. W., …Turner, N. J. (in press). Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases. Chemical Science, 11(19), 5052-5057. https://doi.org/10.1039/d0sc02253e

Chiral primary amines are important intermediates in the synthesis of pharmaceutical compounds. Fungal reductive aminases (RedAms) are NADPH-dependent dehydrogenases that catalyse reductive amination of a range of ketones with short-chain primary ami... Read More about Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases.

Is it time for biocatalysis in fragment-based drug discovery? (2020)
Journal Article
Cosgrove. (2020). Is it time for biocatalysis in fragment-based drug discovery?. Chemical Science, 11104 - 11112. https://doi.org/10.1039/D0SC04103C

The use of biocatalysts for fragment-based drug discovery has yet to be fully investigated, despite the promise enzymes hold for the synthesis of poly-functional, non-protected small molecules. Here we analyze products of the biocatalysis literature... Read More about Is it time for biocatalysis in fragment-based drug discovery?.

One-Pot Synthesis of Chiral N-Arylamines by Combining Biocatalytic Aminations with Buchwald-Hartwig N-Arylation. (2020)
Journal Article
Cosgrove. (2020). One-Pot Synthesis of Chiral N-Arylamines by Combining Biocatalytic Aminations with Buchwald-Hartwig N-Arylation. Angewandte Chemie, 18156 - 18160. https://doi.org/10.1002/anie.202006246

The combination of biocatalysis and chemo-catalysis increasingly offers chemists access to more diverse chemical architectures. Here, we describe the combination of a toolbox of chiral-amine-producing biocatalysts with a Buchwald-Hartwig cross-coupli... Read More about One-Pot Synthesis of Chiral N-Arylamines by Combining Biocatalytic Aminations with Buchwald-Hartwig N-Arylation..

Natural heterogeneous catalysis with immobilised oxidase biocatalysts (2020)
Journal Article
Mattey, A. P., Sangster, J. J., Ramsden, J. I., Baldwin, C., Birmingham, W. R., Heath, R. S., …Flitsch, S. L. (in press). Natural heterogeneous catalysis with immobilised oxidase biocatalysts. RSC advances, 10(33), 19501-19505. https://doi.org/10.1039/d0ra03618h

The generation of immobilised oxidase biocatalysts allowing multifunctional oxidation of valuable chemicals using molecular oxygen is described. Engineered galactose oxidase (GOase) variants M1 and M3–5, an engineered choline oxidase (AcCO6) and mono... Read More about Natural heterogeneous catalysis with immobilised oxidase biocatalysts.

Rapid Model-Based Optimization of a Two-Enzyme System for Continuous Reductive Amination in Flow (2020)
Journal Article
Finnigan, W., Citoler, J., Cosgrove, S. C., & Turner, N. J. (2020). Rapid Model-Based Optimization of a Two-Enzyme System for Continuous Reductive Amination in Flow. Organic Process Research and Development, 24(10), 1969-1977. https://doi.org/10.1021/acs.oprd.0c00075

Enzymes are increasingly combined into multienzyme systems for cost and productivity benefits. Further advantages can be gained through the use of immobilized enzymes, allowing continuous biotransformations in flow. However, the optimization of such... Read More about Rapid Model-Based Optimization of a Two-Enzyme System for Continuous Reductive Amination in Flow.

Biocatalytic Oxidation in Continuous Flow for the Generation of Carbohydrate Dialdehydes (2019)
Journal Article
Cosgrove, S. C., Mattey, A. P., Riese, M., Chapman, M. R., Birmingham, W. R., Blacker, A. J., …Flitsch, S. L. (2019). Biocatalytic Oxidation in Continuous Flow for the Generation of Carbohydrate Dialdehydes. ACS catalysis, 9(12), 11658-11662. https://doi.org/10.1021/acscatal.9b04819

Galactose Oxidase (GOase) has been used for the scalable and selective C-6′ oxidation of lactose, a waste material from the dairy industry. Generation of the 6′-oxo lactose was achieved with full conversion in batch mode at milligram scale, but furth... Read More about Biocatalytic Oxidation in Continuous Flow for the Generation of Carbohydrate Dialdehydes.

Biocatalysis Using Immobilized Enzymes in Continuous Flow for the Synthesis of Fine Chemicals (2018)
Journal Article
Thompson, M. P., Peñafiel, I., Cosgrove, S. C., & Turner, N. J. (2019). Biocatalysis Using Immobilized Enzymes in Continuous Flow for the Synthesis of Fine Chemicals. Organic Process Research and Development, 23(1), 9-18. https://doi.org/10.1021/acs.oprd.8b00305

Biocatalysis has emerged as one of the most promising technologies to enable green synthesis of important chemicals, due to the ambient conditions generally applied for these reactions. Nonetheless, a general uptake of enzymatic transformations has b... Read More about Biocatalysis Using Immobilized Enzymes in Continuous Flow for the Synthesis of Fine Chemicals.

Continuous Flow for the Photochemical C‐H Amination of Arenes (2018)
Journal Article
Cosgrove, S. C., Douglas, G. E., Raw, S. A., & Marsden, S. P. (2018). Continuous Flow for the Photochemical C‐H Amination of Arenes. ChemPhotoChem, 2(10), 851-854. https://doi.org/10.1002/cptc.201800105

The direct C−H amination of arenes by aminium radicals generated by photolysis of N-chloroamines is demonstrated under continuous flow conditions. The reactions proceed with comparable efficiency to small scale batch processes but are superior to lar... Read More about Continuous Flow for the Photochemical C‐H Amination of Arenes.

Radical-mediated direct C–H amination of arenes with secondary amines (2018)
Journal Article
Cosgrove, S. C., Plane, J. M. C., & Marsden, S. P. (2018). Radical-mediated direct C–H amination of arenes with secondary amines. Chemical Science, 9(32), 6647-6652. https://doi.org/10.1039/c8sc01747f

Aryl dialkyl amines, valuable subunits of a wide range of effect chemicals, are accessed by intramolecular amination of aromatic C–H bonds employing UV photolysis of N-chloroamines. The reactions show good functional group tolerance and allow access... Read More about Radical-mediated direct C–H amination of arenes with secondary amines.

Imine Reductases, Reductive Aminases, and Amine Oxidases for the Synthesis of Chiral Amines: Discovery, Characterization, and Synthetic Applications (2018)
Book Chapter
Cosgrove, S. C., Brzezniak, A., France, S. P., Ramsden, J. I., Mangas-Sanchez, J., Montgomery, S. L., …Turner, N. J. (2018). Imine Reductases, Reductive Aminases, and Amine Oxidases for the Synthesis of Chiral Amines: Discovery, Characterization, and Synthetic Applications. In Enzymes in Synthetic Biology (131-149). Elsevier. https://doi.org/10.1016/bs.mie.2018.04.022

Synthesis of the chiral amine moiety is a key challenge for synthetic organic chemistry due to its prevalence in many biologically active molecules. Imine reductase and amine oxidase enzymes have enabled the biocatalytic synthesis of a host of chiral... Read More about Imine Reductases, Reductive Aminases, and Amine Oxidases for the Synthesis of Chiral Amines: Discovery, Characterization, and Synthetic Applications.

Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines (2018)
Journal Article
Cosgrove, S. C., Hussain, S., Turner, N. J., & Marsden, S. P. (2018). Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines. ACS catalysis, 8(6), 5570-5573. https://doi.org/10.1021/acscatal.8b01220

The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)... Read More about Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines.

Highly Productive Oxidative Biocatalysis in Continuous Flow by Enhancing the Aqueous Equilibrium Solubility of Oxygen (2018)
Journal Article
Chapman, M. R., Cosgrove, S. C., Turner, N. J., Kapur, N., & Blacker, A. J. (2018). Highly Productive Oxidative Biocatalysis in Continuous Flow by Enhancing the Aqueous Equilibrium Solubility of Oxygen. Angewandte Chemie International Edition, 57(33), 10535-10539. https://doi.org/10.1002/anie.201803675

We report a simple, mild, and synthetically clean approach to accelerate the rate of enzymatic oxidation reactions by a factor of up to 100 when compared to conventional batch gas/liquid systems. Biocatalytic decomposition of H2O2 is used to produce... Read More about Highly Productive Oxidative Biocatalysis in Continuous Flow by Enhancing the Aqueous Equilibrium Solubility of Oxygen.

Synthesis and organogelating behaviour of amino acid-functionalised triphenylenes (2017)
Journal Article
Meegan, J. E., Yang, X., Rungsirisakun, R., Cosgrove, S. C., Bushby, R. J., Sadeghpour, A., …Ansell, R. J. (in press). Synthesis and organogelating behaviour of amino acid-functionalised triphenylenes. Soft Matter, 13(35), 5922-5932. https://doi.org/10.1039/c7sm00676d

Four novel amino acid-functionalised triphenylenes have been prepared with glycine, L-alanine, L-phenylalanine and L-tryptophan ethyl ester side-chains. The glycine derivative is a good gelator of chloroform, the alanine derivative gels ethanol and t... Read More about Synthesis and organogelating behaviour of amino acid-functionalised triphenylenes.