Skip to main content

Research Repository

Advanced Search

Gavin Miller's Outputs (90)

Tetrasaccharide iteration synthesis of a heparin-like dodecasaccharide and radiolabelling for in vivo tissue distribution studies (2013)
Journal Article
Hansen, S. U., Miller, G. J., Cole, C., Rushton, G., Avizienyte, E., Jayson, G. C., & Gardiner, J. M. (2013). Tetrasaccharide iteration synthesis of a heparin-like dodecasaccharide and radiolabelling for in vivo tissue distribution studies. Nature communications, 4, Article 2016. https://doi.org/10.1038/ncomms3016

Heparin-like oligosaccharides mediate numerous important biological interactions, of which many are implicated in various diseases. Synthetic improvements are central to the development of such oligosaccharides as therapeutics and, in addition, there... Read More about Tetrasaccharide iteration synthesis of a heparin-like dodecasaccharide and radiolabelling for in vivo tissue distribution studies.

Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2-and VEGF(165)-mediated endothelial cell functions (2013)
Journal Article
Miller, G. J., Hansen, S. U., Avizienyte, E., Rushton, G., Cole, C., Jayson, G. C., & Gardiner, J. M. (2013). Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2-and VEGF(165)-mediated endothelial cell functions. Chemical Science, 4(8), 3218 - 3222. https://doi.org/10.1039/C3SC51217G

A concise chemical synthesis of a series of structurally-defined heparin-like oligosaccharides is described. This work provides an efficient entry to octa-, deca-, and dodecasaccharides, including the first synthesis of (GlcNS6S-IdoA2S)5 and (GlcNS6S... Read More about Efficient chemical synthesis of heparin-like octa-, deca- and dodecasaccharides and inhibition of FGF2-and VEGF(165)-mediated endothelial cell functions.

First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide (2012)
Journal Article
Hansen, S. U., Miller, G. J., Jayson, G. C., & Gardiner, J. M. (2013). First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide. Organic Letters, 15(1), 88 - 91. https://doi.org/10.1021/ol303112y

The first example of a gram-scale synthesis of a structurally defined, heparin-related dodecasaccharide is reported. An iterative 14-step process using an iduronate donor disaccharide delivers >1g quantities of the dodecasaccharide sequence [GlcNS-Id... Read More about First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide.

Synthesis and Scalable Conversion of l-Iduronamides to Heparin-Related Di- and Tetrasaccharides (2012)
Journal Article
Miller. (2012). Synthesis and Scalable Conversion of l-Iduronamides to Heparin-Related Di- and Tetrasaccharides. Journal of Organic Chemistry, 7823 -7843. https://doi.org/10.1021/jo300722y

A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel l-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite e... Read More about Synthesis and Scalable Conversion of l-Iduronamides to Heparin-Related Di- and Tetrasaccharides.

A synthesis of C-glycosidic multivalent mannosides suitable for divergent functionalized conjugation (2011)
Journal Article
Miller. (2011). A synthesis of C-glycosidic multivalent mannosides suitable for divergent functionalized conjugation. Tetrahedron Letters, 3216 - 3218. https://doi.org/10.1016/j.tetlet.2011.04.047

Divergent synthesis of two novel C-glycosidic multivalent mannosides derived from a common trivalent C-mannosyl carboxylate-terminated intermediate is described. This illustrates synthesis of multivalent C-glycosidic architectures bearing variable ex... Read More about A synthesis of C-glycosidic multivalent mannosides suitable for divergent functionalized conjugation.

Adaptable Synthesis of C-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization (2010)
Journal Article
Miller. (2010). Adaptable Synthesis of C-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization. Organic Letters, 5262 - 5265. https://doi.org/10.1021/ol102310x

A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic d-mannose, d-glucose, and d-galactose derivatives with different length C1-linked spac... Read More about Adaptable Synthesis of C-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization.

Thieme Chemistry Journal Awardees - Where are They Now? Synthesis of the Marine Glycolipid Dioctadecanoyl Discoside (2009)
Journal Article
Miller. (2009). Thieme Chemistry Journal Awardees - Where are They Now? Synthesis of the Marine Glycolipid Dioctadecanoyl Discoside. SYNLETT, 3099 -3102. https://doi.org/10.1055/s-0029-1218301

The first synthesis of the inositol-containing marine glycolipid dioctadecanoyl discoside is reported. The key glycosylation reaction proceeds with ß-selectivity at reduced temperature. The separable anomers could be readily progressed to afford disc... Read More about Thieme Chemistry Journal Awardees - Where are They Now? Synthesis of the Marine Glycolipid Dioctadecanoyl Discoside.

The 2019 coronavirus (SARS-CoV-2) surface protein (Spike) S1 Receptor Binding Domain undergoes conformational change upon heparin binding
Journal Article
Mycroft-West, C., Su, D., Elli, S., Li, Y., Guimond, S., Miller, G., …Skidmore, M. (2020). The 2019 coronavirus (SARS-CoV-2) surface protein (Spike) S1 Receptor Binding Domain undergoes conformational change upon heparin binding. arXiv, https://doi.org/10.1101/2020.02.29.971093

Many pathogens take advantage of the dependence of the host on the interaction of hundreds of extracellular proteins with the glycosaminoglycans heparan sulphate to regulate homeostasis and use heparan sulphate as a means to adhere and gain access to... Read More about The 2019 coronavirus (SARS-CoV-2) surface protein (Spike) S1 Receptor Binding Domain undergoes conformational change upon heparin binding.