Outputs (81)

Systematic studies toward the synthesis of d -galactosamine-containing coumarin glycosides † (2025)
Journal Article
Wootton, H. S., & Miller, G. J. (2025). Systematic studies toward the synthesis of d -galactosamine-containing coumarin glycosides †. Organic and Biomolecular Chemistry, https://doi.org/10.1039/d5ob00746a

An O-glycosylation method for accessing coumarin glycosides is presented. We report the reaction of 6,8-difluoro-7-hydroxy-4-methylcoumarin and 4-methylumbelliferone with a variety of glycosyl imidate donors using BF3·Et2O as activator to access a se... Read More about Systematic studies toward the synthesis of d -galactosamine-containing coumarin glycosides †.

A modular, reusable biocatalytic flow system for UDP-GlcNAc production (2025)
Journal Article
Roberts, T. L., Dolan, J. P., Miller, G. J., Lima, M. A. D., & Cosgrove, S. C. (2025). A modular, reusable biocatalytic flow system for UDP-GlcNAc production. Reaction Chemistry and Engineering, https://doi.org/10.1039/d5re00127g

We report here the continuous flow synthesis of a high-value sugar nucleotide. Immobilisation of enzymes onto solid carriers permitted transfer of the biocatalysts into packed bed reactors to realise a continuous biocatalytic platform for the synthes... Read More about A modular, reusable biocatalytic flow system for UDP-GlcNAc production.

3′-O-β-Glucosylation of nucleoside analogues using a promiscuous bacterial glycosyltransferase (2025)
Journal Article
Dolan, J. P., Keenan, T., Cheallaigh, A. N., Fascione, M. A., & Miller, G. J. (2025). 3′-O-β-Glucosylation of nucleoside analogues using a promiscuous bacterial glycosyltransferase. RSC Chemical Biology, https://doi.org/10.1039/D5CB00026B

Nucleoside analogue therapeutics have a proven capability within drug discovery as antiviral and antineoplastic agents. However, their efficacy can be limited by poor cellular uptake, off target toxicity and low bioavailability. Glycosylation of phar... Read More about 3′-O-β-Glucosylation of nucleoside analogues using a promiscuous bacterial glycosyltransferase.

3,4,6-Tri-O-acetyl-1-S-acetyl-2-deoxy-2-S-phenylthio-α-d-mannopyranoside (2025)
Journal Article
Porter, J., & Miller, G. J. (2025). 3,4,6-Tri-O-acetyl-1-S-acetyl-2-deoxy-2-S-phenylthio-α-d-mannopyranoside. Molbank, 2025(1), 1-6. https://doi.org/10.3390/M1981

The title compound was isolated as the unexpected reaction product from a reaction attempting to access a glycosyl 1-phosphate. The product was isolated in good yield, as one diastereoisomer, and was characterised by 1H, 13C, and 2D NMR, alongside HR... Read More about 3,4,6-Tri-O-acetyl-1-S-acetyl-2-deoxy-2-S-phenylthio-α-d-mannopyranoside.

Multigram-Scale Synthesis of 2,5-Dideoxy-2,5-imino-d-mannitol (DMDP) and 2,5-Dideoxy-2,5-imino-d-glucitol (DGDP) from d-Fructose and l-Sorbose Using a Regioselective Appel Reaction. (2025)
Journal Article
Sunde-Brown, P., Miller, G. J., & Houston, T. A. (in press). Multigram-Scale Synthesis of 2,5-Dideoxy-2,5-imino-d-mannitol (DMDP) and 2,5-Dideoxy-2,5-imino-d-glucitol (DGDP) from d-Fructose and l-Sorbose Using a Regioselective Appel Reaction. The Journal of Organic Chemistry, 90(6), 2288-2297. https://doi.org/10.1021/acs.joc.4c02667

We report a practical 5 g scale stereoselective synthesis of the valuable iminosugar DMDP from d-fructose in only 7 synthetic steps and in a 70% overall yield, which doubles previously reported yields. This process requires only two chromatographic p... Read More about Multigram-Scale Synthesis of 2,5-Dideoxy-2,5-imino-d-mannitol (DMDP) and 2,5-Dideoxy-2,5-imino-d-glucitol (DGDP) from d-Fructose and l-Sorbose Using a Regioselective Appel Reaction..

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.

Towards the synthesis of a 2-deoxy-2-fluoro-d-mannose building block and characterisation of an unusual 2-S-phenyl anomeric pyridinium triflate salt via 1 → 2 S-migration (2024)
Journal Article
Evans, S. T., Tizzard, G. J., Field, R. A., & Miller, G. J. (2024). Towards the synthesis of a 2-deoxy-2-fluoro-d-mannose building block and characterisation of an unusual 2-S-phenyl anomeric pyridinium triflate salt via 1 → 2 S-migration. Carbohydrate Research, 545, Article 109275. https://doi.org/10.1016/j.carres.2024.109275

Regio- and stereo-selective synthetic routes to 2-deoxy-2-fluoro-d-mannose building blocks are often experimentally challenging when using Selectfluor with the corresponding glycal. We targeted a late-stage method to introduce fluorine in a stereospe... Read More about Towards the synthesis of a 2-deoxy-2-fluoro-d-mannose building block and characterisation of an unusual 2-S-phenyl anomeric pyridinium triflate salt via 1 → 2 S-migration.

Synthesis of Nucleoside Analogs Containing Sulfur or Selenium Replacements of the Ribose Ring Oxygen or Carbon. (2024)
Journal Article
Benckendorff, C. M. M., Sunde-Brown, P., Ní Cheallaigh, A., & Miller, G. J. (2024). Synthesis of Nucleoside Analogs Containing Sulfur or Selenium Replacements of the Ribose Ring Oxygen or Carbon. Journal of Organic Chemistry, 89(23), 16977-16989. https://doi.org/10.1021/acs.joc.4c02409

Nucleoside analogs have proven highly successful in many pharmaceutical intervention strategies, and continued exploration of next generation structural motifs is required. Herein we discuss recent advances toward the chemical synthesis of heteroatom... Read More about Synthesis of Nucleoside Analogs Containing Sulfur or Selenium Replacements of the Ribose Ring Oxygen or Carbon..

Sugar-Coated: Can Multivalent Glycoconjugates Improve upon Nature’s Design? (2024)
Journal Article
Leslie, K. G., Berry, S. S., Miller, G. J., & Mahon, C. S. (2024). Sugar-Coated: Can Multivalent Glycoconjugates Improve upon Nature’s Design?. Journal of the American Chemical Society, 146(40), 27215-27232. https://doi.org/10.1021/jacs.4c08818

Multivalent interactions between receptors and glycans play an important role in many different biological processes, including pathogen infection, self-recognition, and the immune response. The growth in the number of tools and techniques toward the... Read More about Sugar-Coated: Can Multivalent Glycoconjugates Improve upon Nature’s Design?.

Benzoylation of Tetrols: A Comparison of Regioselectivity Patterns for O- and S-Glycosides of d-Galactose (2024)
Journal Article
Porter, J., Roberts, J., & Miller, G. J. (in press). Benzoylation of Tetrols: A Comparison of Regioselectivity Patterns for O- and S-Glycosides of d-Galactose. Journal of Organic Chemistry, https://doi.org/10.1021/acs.joc.4c01508

Efficient protecting group strategies are important for glycan synthesis and represent a unique synthetic challenge in differentiating sugar ring hydroxyl groups. Direct methods to enable regioselective protecting group installation are thus desirabl... Read More about Benzoylation of Tetrols: A Comparison of Regioselectivity Patterns for O- and S-Glycosides of d-Galactose.