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Exploring a glycosylation methodology for the synthesis of hydroxamate-modified alginate building blocks (2019)
Journal Article
Dimitriou, E., & Miller, G. (2019). Exploring a glycosylation methodology for the synthesis of hydroxamate-modified alginate building blocks. Organic and Biomolecular Chemistry, 17(42), 9321-9335. https://doi.org/10.1039/c9ob02053e

Alginate, an anionic polysaccharide, is an important industrial biomaterial naturally harvested from seaweed. Many of its important physicochemical properties derive from the presence of charged carboxylate groups presented as uronic acids within the... Read More about Exploring a glycosylation methodology for the synthesis of hydroxamate-modified alginate building blocks.

Chemical and enzymatic synthesis of the alginate sugar nucleotide building block: GDP-d-mannuronic acid (2019)
Journal Article
Beswick, L., Ahmadipour, S., Dolan, J. P., Rejzek, M., Field, R. A., & Miller, G. J. (2019). Chemical and enzymatic synthesis of the alginate sugar nucleotide building block: GDP-d-mannuronic acid. Carbohydrate Research, 485(1), 107819 -107819. https://doi.org/10.1016/j.carres.2019.107819

Highlights Sugarnucleotide synthesis. Chemical and enzymatic access to GDP-d-ManA. Evaluation of protected and free uronate 1-phosphates for pyrophosphorylation.

6R/S-deutero-a-d-mannopyranoside 1-phosphate (2019)
Journal Article
Miller, G., & Ahmadipour, S. (2019). 6R/S-deutero-a-d-mannopyranoside 1-phosphate. Molbank, 2019(3), Article M1068. https://doi.org/10.3390/M1068

6R/S-deutero-a-d-mannopyranoside 1-phosphate was synthesised from a C6 aldehydic mannose thioglycoside donor in four steps. Using NaBD4 as the reductant, isotopic enrichment at C6 was achieved and the resultant C6-deuterated material was converted th... Read More about 6R/S-deutero-a-d-mannopyranoside 1-phosphate.

Chemoenzymatic Synthesis of C6-Modified Sugar Nucleotides To Probe the GDP-d-Mannose Dehydrogenase from Pseudomonas aeruginosa (2019)
Journal Article
Ahmadipour, S., Pergolizzi, G., Rejzek, M., Field, R. A., & Miller, G. J. (2019). Chemoenzymatic Synthesis of C6-Modified Sugar Nucleotides To Probe the GDP-d-Mannose Dehydrogenase from Pseudomonas aeruginosa. Organic Letters, 21(12), 4415-4419. https://doi.org/10.1021/acs.orglett.9b00967

The chemoenzymatic synthesis of a series of C6-modified GDP-d-Man sugar nucleotides is described. This provides the first structure–function tools for the GDP-d-ManA producing GDP-d-mannose dehydrogenase (GMD) from Pseudomonas aeruginosa. Using a com... Read More about Chemoenzymatic Synthesis of C6-Modified Sugar Nucleotides To Probe the GDP-d-Mannose Dehydrogenase from Pseudomonas aeruginosa.

Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold (2018)
Journal Article
Dimitriou, E., Jones, R., Pritchard, R., Miller, G., & O'Brien, M. (2018). Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold. Tetrahedron, 74(47), 6795-6803. https://doi.org/10.1016/j.tet.2018.09.025

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene s... Read More about Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold.

Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases (2018)
Journal Article
Ahmadipour, S., Beswick, L., & Miller, G. (2018). Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases. Carbohydrate Research, 469, 38 - 47. https://doi.org/10.1016/j.carres.2018.09.002

Sugar-nucleotides are imperative to carbohydrate metabolism and glycoconjugate biosynthesis. Enzymatic methods to access these key materials offer a powerful alternative to traditional chemical synthesis routes. Herein we review recent advances in th... Read More about Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases.

Chapter 18: Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α,β-d- glucopyranose Using the Diazo-Transfer Reagent Imidazole-1- sulfonyl Azide Hydrogen Sulfate By Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller (2018)
Journal Article
Potter, G. T., Jayson, G. C., Gardiner, J. M., Guazelli, L., & Miller, G. (2018). Chapter 18: Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α,β-d- glucopyranose Using the Diazo-Transfer Reagent Imidazole-1- sulfonyl Azide Hydrogen Sulfate By Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller. Journal of Carbohydrate Chemistry, 37(3), 178-178. https://doi.org/10.1080/07328303.2018.1455390

D-Glucosamine, and derivatives thereof, are found in many biologically important saccharides, including glycosaminoglycans (GAGs), and in various classes of oligosaccharides. Glucosamines can also serve as useful chirons. Consequently, synthetic deri... Read More about Chapter 18: Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α,β-d- glucopyranose Using the Diazo-Transfer Reagent Imidazole-1- sulfonyl Azide Hydrogen Sulfate By Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller.

1,2,3,4-Tetra-O-Acetyl- ß-D-Mannuronic Acid (2017)
Journal Article
Miller, G., & Beswick, L. (2017). 1,2,3,4-Tetra-O-Acetyl- ß-D-Mannuronic Acid. Molbank, 2017(3), Article M947. https://doi.org/10.3390/M947

1,2,3,4-Tetra-O-acetyl--D-mannuronic acid was synthesized in three steps from commercial D-mannose in 21% yield. Regioselective 6-O-tritylation followed by per-acetylation and 6-OTr removal using HBr/AcOH gave the required primary alcohol substrate,... Read More about 1,2,3,4-Tetra-O-Acetyl- ß-D-Mannuronic Acid.