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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>.

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.

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.

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.

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.