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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.

Synthetic Site-Selectively Mono-6-O-Sulfated Heparan Sulfate Dodecasaccharide Shows Anti-Angiogenic Properties In Vitro and Sensitizes Tumors to Cisplatin In Vivo (2016)
Journal Article
Miller. (2016). Synthetic Site-Selectively Mono-6-O-Sulfated Heparan Sulfate Dodecasaccharide Shows Anti-Angiogenic Properties In Vitro and Sensitizes Tumors to Cisplatin In Vivo. PloS one, e0159739 -?. https://doi.org/10.1371/journal.+pone.0159739

Heparan sulphate (HS), a ubiquitously expressed glycosaminoglycan (GAG), regulates multiple cellular functions by mediating interactions between numerous growth factors and their cell surface cognate receptors. However, the structural specificity of... Read More about Synthetic Site-Selectively Mono-6-O-Sulfated Heparan Sulfate Dodecasaccharide Shows Anti-Angiogenic Properties In Vitro and Sensitizes Tumors to Cisplatin In Vivo.

Synthetic Site-Selectively Mono-6-<i>O</i>-Sulfated Heparan Sulfate Dodecasaccharide Shows Anti-Angiogenic Properties <i>In Vitro</i> and Sensitizes Tumors to Cisplatin <i>In Vivo</i> (2016)
Journal Article
Avizienyte, E., Cole, C. L., Rushton, G., Miller, G. J., Bugatti, A., Presta, M., …Jayson, G. C. (2016). Synthetic Site-Selectively Mono-6-O-Sulfated Heparan Sulfate Dodecasaccharide Shows Anti-Angiogenic Properties In Vitro and Sensitizes Tumors to Cisplatin In Vivo. PloS one, 11(8), Article ARTN e0159739. https://doi.org/10.1371/journal.pone.0159739

Heparan sulphate (HS), a ubiquitously expressed glycosaminoglycan (GAG), regulates multiple cellular functions by mediating interactions between numerous growth factors and their cell surface cognate receptors. However, the structural specificity of... Read More about Synthetic Site-Selectively Mono-6-<i>O</i>-Sulfated Heparan Sulfate Dodecasaccharide Shows Anti-Angiogenic Properties <i>In Vitro</i> and Sensitizes Tumors to Cisplatin <i>In Vivo</i>.

An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate (2016)
Journal Article
Potter, G. T., Jayson, G. C., Miller, G. J., & Gardiner, J. M. (2016). An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate. Journal of Organic Chemistry, 81(8), 3443-3446. https://doi.org/10.1021/acs.joc.6b00177

Imidazole-1-sulfonyl azide and salts thereof are valuable reagents for diazo-transfer reactions, most particularly conversion of primary amines to azides. The parent reagent and its HCl salt present stability and detonation risks, but the hydrogen su... Read More about An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate.

A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides (2015)
Journal Article
Miller, Miller, G. J., Broberg, K. R., Rudd, C., Helliwell, M. R., Jayson, G. C., & Gardiner, J. M. (2015). A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides. Organic and Biomolecular Chemistry, 13(46), 11208-11219. https://doi.org/10.1039/c5ob01706h

D-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important g... Read More about A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides.

Making the longest sugars: a chemical synthesis of heparin-related [4](n) oligosaccharides from 16-mer to 40-mer (2015)
Journal Article
Hansen, S. U., Miller, G. J., Cliff, M. J., Jayson, G. C., & Gardiner, J. M. (2015). Making the longest sugars: a chemical synthesis of heparin-related [4](n) oligosaccharides from 16-mer to 40-mer. Chemical Science, 6(11), 6158 - 6164. https://doi.org/10.1039/C5SC02091C

The chemical synthesis of long oligosaccharides remains a major challenge. In particular, the synthesis of glycosaminoglycan (GAG) oligosaccharides belonging to the heparin and heparan sulfate (H/HS) family has been a high profile target, particularl... Read More about Making the longest sugars: a chemical synthesis of heparin-related [4](n) oligosaccharides from 16-mer to 40-mer.

Synthetic heparan sulfate dodecasaccharides reveal single sulfation site interconverts CXCL8 and CXCL12 chemokine biology (2015)
Journal Article
Jayson, G. C., Hansen, S. U., Miller, G. J., Cole, C. L., Rushton, G., Avizienytea, E., & Gardiner, J. M. (2015). Synthetic heparan sulfate dodecasaccharides reveal single sulfation site interconverts CXCL8 and CXCL12 chemokine biology. Chemical Communications, 51(72), 13846 -13849. https://doi.org/10.1039/c5cc05222j

he multigram-scale synthesis of a sulfation-site programmed heparin-like dodecasaccharide is described. Evaluation alongside dodecasaccharides lacking this single glucosamine O6-sulfation, or having per-O6-sulfation, shows that site-specific modifica... Read More about Synthetic heparan sulfate dodecasaccharides reveal single sulfation site interconverts CXCL8 and CXCL12 chemokine biology.

Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids (2015)
Journal Article
Potter, G. T., Jayson, G. C., Miller, G. J., & Gardiner, J. M. (2015). Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids. Tetrahedron Letters, 56(37), 5153 - 5156. https://doi.org/10.1016/j.tetlet.2015.05.054

A series of aromatic and heteroaromatic primary amides were converted directly to carboxylic acids by heating with amyl nitrite in acetic acid. Most conversions proceeded to give reasonable to excellent yields on a range of substrates containing vari... Read More about Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids.

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., …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., …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., Sezaki, T., Kusamori, K., …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.