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Synthesis of S-Glycoside Building Blocks as Mimetics of the Repeating d-GlcN-α-1,4-d-GlcA Heparan Sulfate Disaccharide (2024)
Journal Article
O’Shea, C., & Miller, G. J. (2024). Synthesis of S-Glycoside Building Blocks as Mimetics of the Repeating d-GlcN-α-1,4-d-GlcA Heparan Sulfate Disaccharide. Molecules, 29(23), Article 5809. https://doi.org/10.3390/molecules29235809

Heparan sulfate (HS), a sulfated linear carbohydrate that decorates the cell surface and extracellular matrix, is a key regulator of biological processes. Owing to the inherent structural complexity of HS, structure-to-function studies with its ligan... Read More about Synthesis of S-Glycoside Building Blocks as Mimetics of the Repeating d-GlcN-α-1,4-d-GlcA Heparan Sulfate Disaccharide.

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., …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 †.

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., …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. (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., Chagnault, V., Nader, H., …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..

Design, chemical synthesis and antiviral evaluation of 2'-deoxy-2'-fluoro-2'-C-methyl-4'-thionucleosides. (2022)
Journal Article
Guinan, M., Huang, N., Smith, M., & Miller, G. (2022). Design, chemical synthesis and antiviral evaluation of 2'-deoxy-2'-fluoro-2'-C-methyl-4'-thionucleosides. Bioorganic and Medicinal Chemistry Letters, 61, Article 128605. https://doi.org/10.1016/j.bmcl.2022.128605

Nucleoside analogues represent an historically accomplished class of antiviral drug. Notwithstanding this, new molecular scaffolds are required to overcome their limitations and evolve pharmacophore space within this established field. Herein, we dev... Read More about Design, chemical synthesis and antiviral evaluation of 2'-deoxy-2'-fluoro-2'-C-methyl-4'-thionucleosides..

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.

Chemical synthesis of 4′-thio and 4′-sulfinyl pyrimidine nucleoside analogues (2021)
Journal Article
Guinan, M., Huang, N., Hawes, C. S., Lima, M. A., Smith, M., & Miller, G. J. (2021). Chemical synthesis of 4′-thio and 4′-sulfinyl pyrimidine nucleoside analogues. Organic and Biomolecular Chemistry, 20(7), 1401-1406. https://doi.org/10.1039/d1ob02097h

Analogues of the canonical nucleosides required for nucleic acid synthesis have a longstanding presence and proven capability within antiviral and anticancer research. 4'-Thionucleosides, that incorporate bioisosteric replacement of furanose oxygen w... Read More about Chemical synthesis of 4′-thio and 4′-sulfinyl pyrimidine nucleoside analogues.

Prospects for anti-Candida therapy through targeting the cell wall: A mini-review (2021)
Journal Article
Ahmadipour, S., Field, R. A., & Miller, G. (2021). Prospects for anti-Candida therapy through targeting the cell wall: A mini-review. The Cell Surface, 7, Article 100063. https://doi.org/10.1016/j.tcsw.2021.100063

The impact of fungal infections on humans is a serious public health issue that has received much less attention than bacterial infection and treatment, despite ever-increasing incidence exacerbated by an increased incidence of immunocompromised indi... Read More about Prospects for anti-Candida therapy through targeting the cell wall: A mini-review.

Developments in the Chemical Synthesis of Heparin and Heparan Sulfate (2021)
Journal Article
Pongener, I., O'Shea, C., Wootton, H., Watkinson, M., & Miller, G. J. (2021). Developments in the Chemical Synthesis of Heparin and Heparan Sulfate. Chemical Record, 21(11), 3238-3255. https://doi.org/10.1002/tcr.202100173

Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further underst... Read More about Developments in the Chemical Synthesis of Heparin and Heparan Sulfate.

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate (2021)
Journal Article
Dimitriou, E., & Miller, G. (2021). Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate. Beilstein Journal of Organic Chemistry, 1527 - 1532. https://doi.org/10.3762/bjoc.17.110

<jats:p>Alginate is a biocompatible and industrially relevant polysaccharide that derives many of its important properties from the charged carboxylate groups within its polyuronic acid backbone. The design and inclusion of isosteric replacements for... Read More about Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate.

Glycosaminoglycans from Litopenaeus vannamei Inhibit the Alzheimer’s Disease ß Secretase, BACE1 (2021)
Journal Article
Mycroft-West, C. J., Devlin, A. J., Cooper, L. C., Guimond, S. E., Procter, P., Guerrini, M., …Skidmore, M. A. (2021). Glycosaminoglycans from Litopenaeus vannamei Inhibit the Alzheimer’s Disease ß Secretase, BACE1. Marine Drugs, 19(4), 203 -203. https://doi.org/10.3390/md19040203

Only palliative therapeutic options exist for the treatment of Alzheimer’s Disease; no new successful drug candidates have been developed in over 15 years. The widely used clinical anticoagulant heparin has been reported to exert beneficial effects t... Read More about Glycosaminoglycans from Litopenaeus vannamei Inhibit the Alzheimer’s Disease ß Secretase, BACE1.

Illuminating glycoscience: synthetic strategies for FRET-enabled carbohydrate active enzyme probes (2020)
Journal Article
Singh, M., Watkinson, M., Scanlan, E. M., & Miller, G. (2020). Illuminating glycoscience: synthetic strategies for FRET-enabled carbohydrate active enzyme probes. RSC Chemical Biology, 5(1), 352 - 368

Carbohydrates are synthesised, refined and degraded by carbohydrate active enzymes. FRET is emerging as a powerful tool to monitor and quantify their activity as well as to test inhibitors as new drug candidates and monitor disease.

Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block (2020)
Journal Article
Dimitriou, E., & Miller, G. (2020). Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block. Molbank, 2020(1), M1111. https://doi.org/10.3390/M1111

Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-&alpha;-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulph... Read More about Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block.