Outputs (4)

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.