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Gavin Miller's Outputs (96)

Modular Synthesis of Heparin-Related Tetra-, Hexa- and Octasaccharides with Differential O-6 Protections: Programming for Regiodefined 6-O-Modifications (2015)
Journal Article
Baráth, M., Hansen, S. U., Dalton, C. E., Jayson, G. C., Miller, G. J., & Gardiner, J. M. (2015). Modular Synthesis of Heparin-Related Tetra-, Hexa- and Octasaccharides with Differential O-6 Protections: Programming for Regiodefined 6-O-Modifications. Molecules, 20(4), 6167 - 6180. https://doi.org/10.3390/molecules20046167

Heparin and heparan sulphate (H/HS) are important members of the glycosaminoglycan family of sugars that regulate a substantial number of biological processes. Such biological promiscuity is underpinned by hetereogeneity in their molecular structure.... Read More about Modular Synthesis of Heparin-Related Tetra-, Hexa- and Octasaccharides with Differential O-6 Protections: Programming for Regiodefined 6-O-Modifications.

Synthesis of L-Iduronic Acid Derivatives via [3.2.1] and [2.2.2] L-Iduronic Lactones from Bulk Glucose-Derived Cyanohydrin Hydrolysis: A Reversible Conformationally Switched Superdisarmed/Rearmed Lactone Route to Heparin Disaccharides (2015)
Journal Article
Hansen, S. U., Dalton, C. E., Baráth, M., Kwan, G., Raftery, J., Jayson, G. C., Miller, G. J., & Gardiner, J. M. (2015). Synthesis of L-Iduronic Acid Derivatives via [3.2.1] and [2.2.2] L-Iduronic Lactones from Bulk Glucose-Derived Cyanohydrin Hydrolysis: A Reversible Conformationally Switched Superdisarmed/Rearmed Lactone Route to Heparin Disaccharides. Journal of Organic Chemistry, 80(8), 3777 -3789. https://doi.org/10.1021/jo502776f

l-Idofuranoside cyanohydrin 1 is converted on large scale into a mixture of l-IdoA methyl pyranosides and furanosides, which is converged to provide short 2-step routes to bicyclic [3.2.1] or [2.2.2] l-iduronate lactones. The former is obtained via a... Read More about Synthesis of L-Iduronic Acid Derivatives via [3.2.1] and [2.2.2] L-Iduronic Lactones from Bulk Glucose-Derived Cyanohydrin Hydrolysis: A Reversible Conformationally Switched Superdisarmed/Rearmed Lactone Route to Heparin Disaccharides.

The development of anti-angiogenic heparan sulfate oligosaccharides (2014)
Journal Article
Jayson, G. C., Miller, G. J., Hansen, S. U., Barath, M., Gardiner, J. M., & Avizienyte, E. (2014). The development of anti-angiogenic heparan sulfate oligosaccharides. Biochemical Society Transactions, 42(6), 1596 -1600. https://doi.org/10.1042/BST20140229

Angiogenesis has emerged as a novel target for anti-cancer therapies through randomized clinical trials that tested the benefit of adding vascular endothelial growth factor (VEGF) inhibitors to conventional cytotoxic therapies. However, despite impro... Read More about The development of anti-angiogenic heparan sulfate oligosaccharides.

Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy (2014)
Journal Article
Miller, G. J., Hansen, S. U., Baráth, M., Johannessen, C., Blanch, E. W., Jayson, G. C., & Gardiner, J. M. (2014). Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy. Carbohydrate Research, 400, 44 -53. https://doi.org/10.1016/j.carres.2014.06.026

Synthesis of an array of differentially sulfated GlcN–IdoA disaccharides, accessible on good scale, directly from l-iduronate components is described. These are specifically directed to provide the sulfation variability at the key most common biologi... Read More about Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy.

Selection of a novel anti-nicotine vaccine: influence of antigen design on antibody function in mice (2013)
Journal Article
Pryde, D. C., Jones, L. H., Gervais, D. P., Stead, D. R., Blakemore, D. C., Selby, M. D., Brown, A. D., Coe, J. W., Badland, M., Beal, D. M., Glen, R., Wharton, Y., Miller, G. J., White, P., Zhang, N., Benoit, M., Robertson, K., Merson, J. R., Davis, H. L., & McCluskie, M. J. (2013). Selection of a novel anti-nicotine vaccine: influence of antigen design on antibody function in mice. PloS one, 8(10), Article e76557. https://doi.org/10.1371/journal.pone.0076557

Anti-nicotine vaccines may aid smoking cessation via the induction of anti-nicotine antibodies (Ab) which reduce nicotine entering the brain, and hence the associated reward. Ab function depends on both the quantity (titer) and the quality (affinity)... Read More about Selection of a novel anti-nicotine vaccine: influence of antigen design on antibody function in mice.

Small-Molecule-Induced Clustering of Heparan Sulfate Promotes Cell Adhesion (2013)
Journal Article
Takemoto, N., Suehara, T., Frisco, H. L., Sato, S.-I., Sezaki, T., Kusamori, K., Kawazoe, Y., Min Park, S., Yamazoe, S., Mizuhata, Y., Inoue, R., Miller, G. J., Hansen, S. U., Jayson∥, G. C., Gardiner, J. M., Kanaya, T., Tokitoh, N., Ueda, K., Takakura, Y., Kioka, N., …Uesugi, M. (2013). Small-Molecule-Induced Clustering of Heparan Sulfate Promotes Cell Adhesion. Journal of the American Chemical Society, 135(30), 11032 -11039. https://doi.org/10.1021/ja4018682

Adhesamine is an organic small molecule that promotes adhesion and growth of cultured human cells by binding selectively to heparan sulfate on the cell surface. The present study combined chemical, physicochemical, and cell biological experiments, us... Read More about Small-Molecule-Induced Clustering of Heparan Sulfate Promotes Cell Adhesion.

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.

Heparin inhibits cellular invasion by SARS-CoV-2: structural dependence of the interaction of the surface protein (spike) S1 receptor binding domain with heparin
Other
Mycroft-West, C. J., Su, D., Pagani, I., Rudd, T. R., Elli, S., Guimond, S. E., Miller, G., Meneghetti, M. C. Z., Nader, H. B., Li, Y., Nunes, Q. M., Procter, P., Mancini, N., Clementi, M., Bisio, A., Forsyth, N. R., Turnbull, J. E., Guerrini, M., Fernig, D. G., Vicenzi, E., …Skidmore, M. A. Heparin inhibits cellular invasion by SARS-CoV-2: structural dependence of the interaction of the surface protein (spike) S1 receptor binding domain with heparin

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., Turnbull, J., Yates, E., Guerrini, M., Fernig, D., Lima, M., & 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.