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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., Skidmore, M. A., Miller, G. J., & Cosgrove, S. C. (2023). Harnessing a Biocatalyst to Bioremediate the Purification of Alkylglycosides. ChemBioChem, Article e202300752. https://doi.org/10.1002/cbic.202300625

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.

A transcriptomics-based drug repositioning approach to identify drugs with similar activities for the treatment of muscle pathologies in spinal muscular atrophy (SMA) models. (2023)
Journal Article
Hoolachan, J. M., McCallion, E., Sutton, E. R., Çetin, Ö., Pacheco-Torres, P., Dimitriadi, M., Sari, S., Miller, G. J., Okoh, M., Walter, L. M., Claus, P., Wood, M. J., Tonge, D., & Bowerman, M. (2024). A transcriptomics-based drug repositioning approach to identify drugs with similar activities for the treatment of muscle pathologies in spinal muscular atrophy (SMA) models. Human molecular genetics, 33(5), 400–425. https://doi.org/10.1093/hmg/ddad192

Spinal muscular atrophy (SMA) is a genetic neuromuscular disorder caused by the reduction of survival of motor neuron (SMN) protein levels. Although three SMN-augmentation therapies are clinically approved that significantly slow down disease progres... Read More about A transcriptomics-based drug repositioning approach to identify drugs with similar activities for the treatment of muscle pathologies in spinal muscular atrophy (SMA) models..

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., Skidmore, M. A., Miller, G. J., & 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..

Reverse thiophosphorylase activity of a glycoside phosphorylase in the synthesis of an unnatural Manβ1,4GlcNAc library † (2023)
Journal Article
Keenan, T., Hatton, N. E., Porter, J., Vendeville, J.-B., Wheatley, D. E., Ghirardello, M., Wahart, A. J. C., Ahmadipour, S., Walton, J., Galan, M. C., Linclau, B., Miller, G. J., & Fascione, M. A. (in press). Reverse thiophosphorylase activity of a glycoside phosphorylase in the synthesis of an unnatural Manβ1,4GlcNAc library †. Chemical Science, 14(42), 11638-11646. https://doi.org/10.1039/d3sc04169g

β-Mannosides are ubiquitous in nature, with diverse roles in many biological processes. Notably, Manβ1,4GlcNAc a constituent of the core N-glycan in eukaryotes was recently identified as an immune activator, highlighting its potential for use in immu... Read More about Reverse thiophosphorylase activity of a glycoside phosphorylase in the synthesis of an unnatural Manβ1,4GlcNAc library †.

Preparation of a 4′‐Thiouridine Building‐Block for Solid‐Phase Oligonucleotide Synthesis (2023)
Journal Article
Benckendorff, C. M. M., Sanghvi, Y. S., & Miller, G. J. (2023). Preparation of a 4′‐Thiouridine Building‐Block for Solid‐Phase Oligonucleotide Synthesis. Current Protocols in Neuroscience, 3(9), Article e878. https://doi.org/10.1002/cpz1.878

Starting from a commercially available thioether, we report a nine‐step synthesis of a 4′‐thiouridine phosphoramidite building‐block. We install the uracil nucleobase using Pummerer‐type glycosylation of a sulfoxide intermediate followed by a series... Read More about Preparation of a 4′‐Thiouridine Building‐Block for Solid‐Phase Oligonucleotide Synthesis.

Virtual screening, identification and in vitro validation of small molecule GDP-mannose dehydrogenase inhibitors † (2023)
Journal Article
Dolan, J., Ahmadipour, S., Wahart, A., Ni Cheallaigh, A., Sari, S., Eurtivong,, C., Lima, M., Skidmore, M., Volcho, K., Reynisson, J., Field, R., & Miller, G. (2023). Virtual screening, identification and in vitro validation of small molecule GDP-mannose dehydrogenase inhibitors †. RSC Chemical Biology, 4(11), 865-870. https://doi.org/10.1039/D3CB00126A

Upon undergoing mucoid conversion within the lungs of cystic fibrosis patients, the pathogenic bacterium Pseudomonas aeruginosa synthesises copious quantities of the virulence factor and exopolysaccharide alginate. The enzyme guanosine diphosphate ma... Read More about Virtual screening, identification and in vitro validation of small molecule GDP-mannose dehydrogenase inhibitors †.

Indolo[2,3- e ]benzazocines and indolo[2,3- f ]benzazonines and their copper( ii ) complexes as microtubule destabilizing agents † (2023)
Journal Article
Wittmann, C., Dömötör, O., Kuznetcova, I., Spengler, G., Reynisson, J., Holder, L., Miller, G. J., Enyedy, E. A., Bai, R., Hamel, E., & Arion, V. B. (2023). Indolo[2,3- e ]benzazocines and indolo[2,3- f ]benzazonines and their copper( ii ) complexes as microtubule destabilizing agents †. Dalton Transactions, 52(29), 9964-9982. https://doi.org/10.1039/d3dt01632c

A series of four indolo[2,3-e]benzazocines HL1–HL4 and two indolo[2,3-f]benzazonines HL5 and HL6, as well as their respective copper(ii) complexes 1–6, were synthesized and characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry, single c... Read More about Indolo[2,3- e ]benzazocines and indolo[2,3- f ]benzazonines and their copper( ii ) complexes as microtubule destabilizing agents †.

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.

Chemical Diversification of Carbocyclic Fluorinated Pyrimidine Nucleosides: Introducing 2'-Arabino Analogues and Ring Unsaturation (2023)
Journal Article
Benckendorff, C. M. M., Hawes, C. S., Smith, M., & Miller, G. J. (2023). Chemical Diversification of Carbocyclic Fluorinated Pyrimidine Nucleosides: Introducing 2'-Arabino Analogues and Ring Unsaturation. SYNLETT, 35(06), 659-664. https://doi.org/10.1055/a-2079-9310

Analogues of the canonical nucleosides have a longstanding presence and proven capability within medicinal chemistry and drug-discovery research. Herein, we report chemical diversification of carbocyclic pyrimidine nucleosides containing CF2 and CHF... Read More about Chemical Diversification of Carbocyclic Fluorinated Pyrimidine Nucleosides: Introducing 2'-Arabino Analogues and Ring Unsaturation.

Chemical synthesis of amphiphilic glycoconjugates: Access to amino, fluorinated and sulfhydryl oleyl glucosides. (2023)
Journal Article
Porter, J., Parisi, D., Miller, T., Cheallaigh, A. N., & Miller, G. J. (2023). Chemical synthesis of amphiphilic glycoconjugates: Access to amino, fluorinated and sulfhydryl oleyl glucosides. Carbohydrate Research, 530, Article 108854. https://doi.org/10.1016/j.carres.2023.108854

Amphiphilic glycoconjugates offer an important prospect for development as chemical biology tools and biosurfactants. The chemical synthesis of such materials is required to expedite such prospect, compounded by the example of oleyl glycosides. Herei... Read More about Chemical synthesis of amphiphilic glycoconjugates: Access to amino, fluorinated and sulfhydryl oleyl glucosides..

A sulphated glycosaminoglycan extract from Placopecten magellanicus inhibits the Alzheimer's disease ß-site amyloid precursor protein cleaving enzyme 1 (BACE-1). (2023)
Journal Article
Mycroft-West, C., Devlin, A., Cooper, L., Guimond, S., Procter, P., Miller, G., Guerrini, M., Fernig, D., Yates, E., Andrade De Lima, M., & Skidmore, M. (2023). A sulphated glycosaminoglycan extract from Placopecten magellanicus inhibits the Alzheimer's disease ß-site amyloid precursor protein cleaving enzyme 1 (BACE-1). Carbohydrate Research, 525, Article 108747. https://doi.org/10.1016/j.carres.2023.108747

The clinically important anticoagulant heparin, a member of the glycosaminoglycan family of carbohydrates that is extracted predominantly from porcine and bovine tissue sources, has previously been shown to inhibit the ß-site amyloid precursor protei... Read More about A sulphated glycosaminoglycan extract from Placopecten magellanicus inhibits the Alzheimer's disease ß-site amyloid precursor protein cleaving enzyme 1 (BACE-1)..

Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. (2023)
Journal Article
Porter, J., Lima, M. A., Pongener, I., & Miller, G. (2023). Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. Carbohydrate Research, 524, Article 108759. https://doi.org/10.1016/j.carres.2023.108759

Sulfur containing glycosides offer an exciting prospect for inclusion within noncanonical glycan sequences, particularly as enabling probes for chemical glycobiology and for carbohydrate-based therapeutic development. In this context, we required acc... Read More about Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose..

Biocatalytic Approaches to Building Blocks for Enzymatic and Chemical Glycan Synthesis (2022)
Journal Article
Cosgrove, Miller, & Dolan, J. (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.

Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues (2022)
Journal Article
Benckendorff, C., Slyusarchuk, V. D., Huang, N., Lima, M. A., Smith, M., & Miller, G. J. (2022). Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues. Organic and Biomolecular Chemistry, 20(47), 9469 - 9489. https://doi.org/10.1039/D2OB01761J

Analogues of the canonical nucleosides have a longstanding presence and proven capability within medicinal chemistry and drug discovery research. The synthesis reported herein successfully replaces furanose oxygen with CF2 and CHF in pyrimidine nucle... Read More about Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues.

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase. (2022)
Journal Article
Ahmadipour, S., Wahart, A., Dolan, J., Beswick, L., Hawes, C., Field, R., & Miller, G. (2022). Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase. Beilstein Journal of Organic Chemistry, 18, 1379 - 1384. https://doi.org/10.3762/bjoc.18.142

Sufferers of cystic fibrosis are at significant risk of contracting chronic bacterial lung infections. The dominant pathogen in these cases is mucoid Pseudomonas aeruginosa. Such infections are characterised by overproduction of the exopolysaccharide... Read More about Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase..

Using NMR to Dissect the Chemical Space and O-Sulfation Effects within the O- and S-Glycoside Analogues of Heparan Sulfate. (2022)
Journal Article
Meneghetti, M., Naughton, L., O'Shea, C., Koffi Teki, D.-E., Chagnault, V., Nader, H., Rudd, T., Yates, E., Kovensky, J., Miller, G., & Andrade De Lima, M. (2022). Using NMR to Dissect the Chemical Space and O-Sulfation Effects within the O- and S-Glycoside Analogues of Heparan Sulfate. ACS Omega, 7(28), 24461 - 24467. https://doi.org/10.1021/acsomega.2c02070

Heparan sulfate (HS), a sulfated linear carbohydrate that decorates the cell surface and extracellular matrix, is ubiquitously distributed throughout the animal kingdom and represents a key regulator of biological processes and a largely untapped res... Read More about Using NMR to Dissect the Chemical Space and O-Sulfation Effects within the O- and S-Glycoside Analogues of Heparan Sulfate..

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..