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

Hansen, Steen U.; Dalton, Charlotte E.; Baráth, Marek; Kwan, Glenn; Raftery, James; Jayson, Gordon C.; Miller, Gavin J.; Gardiner, John M.

doi:10.1021/jo502776f

All Outputs (6)

A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides (2015)
Journal Article

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

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

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

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

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

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.