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Gavin Miller's Outputs (8)

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.

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.

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.

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.