Keele Research Repository

Article

Reihill, M, Fournière, V, Cheallaigh, AN, Edlund, JO, Miller, GJ, Borén, T, Lahmann, M and Oscarson, S (2023) Synthesis of a B-Antigen Hexasaccharide, a B-Lewis b Heptasaccharide and Glycoconjugates Thereof to Investigate Binding Properties of Helicobacter pylori. Chemistry – A European Journal, 29 (16).

Mycroft-West, CJ, Devlin, AJ, Cooper, LC, Guimond, SE ORCID: https://orcid.org/0000-0002-5903-418X, Procter, P, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Guerrini, M, Fernig, DG, Yates, EA, Lima, MA ORCID: https://orcid.org/0000-0002-8952-3080 and Skidmore, MA ORCID: https://orcid.org/0000-0002-0287-5594 (2023) A sulphated glycosaminoglycan extract from Placopecten magellanicus inhibits the Alzheimer's disease β-site amyloid precursor protein cleaving enzyme 1 (BACE-1). Carbohydrate Research, 525 (108747).

Porter, J, Lima, MA, Pongener, I and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2023) Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. Carbohydrate Research, 524 (108759).

Dolan, JP ORCID: https://orcid.org/0000-0002-7009-2225, Cosgrove, SC ORCID: https://orcid.org/0000-0001-9541-7201 and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2022) Biocatalytic Approaches to Building Blocks for Enzymatic and Chemical Glycan Synthesis. JACS Au, 3 (1). pp. 47-61.

Benckendorff, CMM, Slyusarchuk, VD, Huang, N, Lima, MA ORCID: https://orcid.org/0000-0002-8952-3080, Smith, M and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2022) Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues. Organic & Biomolecular Chemistry, 20 (47). 9469 - 9489.

Ahmadipour, S, Wahart, AJC, Dolan, JP, Beswick, L, Hawes, CS, Field, RA and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2022) Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase. Beilstein J Org Chem, 18. 1379 - 1384.

Meneghetti, MCZ, Naughton, L, O'Shea, C, Koffi Teki, DS-E, Chagnault, V, Nader, HB, Rudd, TR, Yates, EA, Kovensky, J, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Lima, MA ORCID: https://orcid.org/0000-0002-8952-3080 (2022) Using NMR to Dissect the Chemical Space and O-Sulfation Effects within the O- and S-Glycoside Analogues of Heparan Sulfate. ACS Omega, 7 (28). 24461 - 24467.

Ahmadipour, S, Wahart, AJC, Dolan, JP, Beswick, L, Hawes, CS ORCID: https://orcid.org/0000-0001-6902-7939, Field, RA and Miller, GJ (2022) Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP‑mannose dehydrogenase. Beilstein Archives.

Guinan, M, Huang, N, Smith, M and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2022) Design, chemical synthesis and antiviral evaluation of 2'-deoxy-2'-fluoro-2'-C-methyl-4'-thionucleosides. Bioorganic & Medicinal Chemistry Letters, 61. 128605 - ?.

Cosgrove, SC ORCID: https://orcid.org/0000-0001-9541-7201 and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2022) Advances in biocatalytic and chemoenzymatic synthesis of nucleoside analogues. Expert Opinion on Drug Discovery, 17 (4). pp. 355-364.

Wahart, AJC, Staniland, J, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Cosgrove, SC ORCID: https://orcid.org/0000-0001-9541-7201 (2022) Oxidase enzymes as sustainable oxidation catalysts. Royal Society Open Science, 9 (1).

Ahmadipour, S, Reynisson, J ORCID: https://orcid.org/0000-0003-4174-9512, Field, RA and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2022) Sweet targets: sugar nucleotide biosynthesis inhibitors. Future Medicinal Chemistry.

Ahmadipour, S, Field, RA and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2021) Prospects for anti-Candida therapy through targeting the cell wall: A mini-review. The Cell Surface, 7. 100063 - 100063.

Guinan, M, Huang, N, Hawes, CS ORCID: https://orcid.org/0000-0001-6902-7939, Lima, MA ORCID: https://orcid.org/0000-0002-8952-3080, Smith, M and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2021) Chemical synthesis of 4'-thio and 4'-sulfinyl pyrimidine nucleoside analogues. Organic & Biomolecular Chemistry.

Pongener, I, O'Shea, C, Wootton, H, Watkinson, M ORCID: https://orcid.org/0000-0003-1877-5667 and Miller, GJ (2021) Developments in the Chemical Synthesis of Heparin and Heparan Sulfate. The Chemical Record, 21 (11). pp. 3238-3255.

Dimitriou, E and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2021) Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate. Beilstein Journal of Organic Chemistry, 17. 1527 - 1532.

Mycroft-West, CJ, Devlin, AJ, Cooper, LC, Guimond, SE, Procter, P, Guerrini, M, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Fernig, DG, Yates, EA, Lima, MA and Skidmore, MA (2021) Glycosaminoglycans from Litopenaeus vannamei Inhibit the Alzheimer’s Disease β Secretase, BACE1. Marine Drugs, 19 (4). 203 -203.

Mycroft-West, CJ, Su, D, Pagani, I, Rudd, TR, Elli, S, Gandhi, NS, Guimond, SE, Miller, GJ, Meneghetti, MCZ, Nader, HB, Li, Y, Nunes, QM, Procter, P, Mancini, N, Clementi, M, Bisio, A, Forsyth, NR ORCID: https://orcid.org/0000-0001-5156-4824, Ferro, V, Turnbull, JE, Guerrini, M, Fernig, DG, Vicenzi, E, Yates, EA, Lima, MA and Skidmore, MA ORCID: https://orcid.org/0000-0002-0287-5594 (2020) Heparin Inhibits Cellular Invasion by SARS-CoV-2: Structural Dependence of the Interaction of the Spike S1 Receptor-Binding Domain with Heparin. Thrombosis and Haemostasis, 120 (12). 1700 - 1715.

Singh, M, Watkinson, M ORCID: https://orcid.org/0000-0003-1877-5667, Scanlan, EM and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2020) Illuminating glycoscience: synthetic strategies for FRET-enabled carbohydrate active enzyme probes. RSC Chemical Biology, 1 (5). 352 - 368.

Ní Cheallaigh, A, Guimond, SE ORCID: https://orcid.org/0000-0002-5903-418X, Oscarson, S and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2020) Chemical synthesis of a sulfated d-glucosamine library and evaluation of cell proliferation capabilities. Carbohydrate Research, 495. 108085 - ?.

Guinan, M, Benckendorff, C, Smith, M and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2020) Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues. Molecules, 25 (9).

Mycroft-West, CJ, Devlin, AJ, Cooper, LC, Procter, P, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Fernig, DG, Guerrini, M, Guimond, SE, Lima, MA, Yates, EA and Skidmore, MA ORCID: https://orcid.org/0000-0002-0287-5594 (2020) Inhibition of BACE1, the β-secretase implicated in Alzheimer's disease, by a chondroitin sulfate extract from Sardina pilchardus. Neural Regeneration Research, 15 (8). 1546 - 1553.

Dimitriou, E and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2020) Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block. Molbank, 2020 (1).

Beswick, L, Ahmadipour, S, Hofman, G-J, Wootton, H, Dimitriou, E, Reynisson, J ORCID: https://orcid.org/0000-0003-4174-9512, Field, RA, Linclau, B and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2019) Exploring anomeric glycosylation of phosphoric acid: Optimisation and scope for non-native substrates. Carbohydrate Research, 488.

Beswick, L, Ahmadipour, S, Dolan, JP, Rejzek, M, Field, RA and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2019) Chemical and enzymatic synthesis of the alginate sugar nucleotide building block: GDP-d-mannuronic acid. Carbohydrate Research, 485. 107819 -107819.

Dimitriou, E and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2019) Exploring a glycosylation methodology for the synthesis of hydroxamate-modified alginate building blocks. Organic & Biomolecular Chemistry, 17 (42). pp. 9321-9335.

Ahmadipour, S and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2019) 6R/S-deutero-α-d-mannopyranoside 1-phosphate. Molbank, 2019 (3). M1068 - M1068.

Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, O'Brien, M, Jones, RH, Dimitriou, E and Pritchard, R (2018) Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold. Tetrahedron, 74 (47). pp. 6795-6803.

Ahmadipour, S, Beswick, L and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2018) Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases. Carbohydrate Research, 469. 38 - 47.

Ahmadipour, S and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2017) Recent advances in the chemical synthesis of sugar-nucleotides. Carbohydrate Research, 451. pp. 95-109.

Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Beswick, L (2017) 1,2,3,4-Tetra-O-Acetyl- β-D-Mannuronic Acid. Molbank, 2017 (3).

Avizienyte, E, Cole, CL, Rushton, G, Miller, GJ, Bugatti, A, Presta, M, Gardiner, JM and Jayson, GC (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). e0159739 -?.

Cheallaigh, A, Potter, G, Gardiner, J and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2016) Preparation of Methyl 1,2,3,4-tetra-O-acetyl-B-D-glucopyranuronate. Organis Syntheses, 93. 200 - 209.

Potter, GT, Jayson, GC, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Gardiner, JM (2015) Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids. Tetrahedron Letters, 56 (37). 5153 - 5156.

Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Broberg, KR, Rudd, C, Helliwell, MR, Jayson, GC and Gardiner, JM (2015) A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides. Organic & Biomolecular Chemistry, 2015 (13). pp. 11208-11219.

Hansen, SU, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Cliff, MJ, Jaysonc, GC and Gardiner, JM (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.

Jayson, GC, Hansen, SU, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Cole, CL, Rushton, G, Avizienyte, E and Gardiner, JM (2015) Synthetic heparan sulfate dodecasaccharides reveal single sulfation site interconverts CXCL8 and CXCL12 chemokine biology. Chemical Communications, 51 (72). 13846 -13849.

Barath, M, Hansen, SU, Dalton, CE, Jayson, GC, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Gardiner, JM (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.

Hansen, SU, Dalton, CE, Barath, M, Kwan, G, Raftery, J, Jayson, GC, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Gardiner, JM (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.

Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Hansen, SU, Barath, M, Johannessen, C, Blanch, EW, Jayson, GC and Gardiner, JM (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.

Jayson, GC, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Hansen, SU, Barath, M, Gardiner, JM and Avizienyte, E (2014) The development of anti-angiogenic heparan sulfate oligosaccharides. Biochemical Society Transactions, 42 (6). 1596 -1600.

Pryde, DC, Jones, LH, Gervais, DP, Stead, DR, Blakemore, DC, Selby, MD, Brown, AD, Coe, JW, Badland, M, Beal, DM, Glen, R, Wharton, Y, Miller, GJ, White, P, Zhang, N, Benoit, M, Robertson, K, Merson, JR, Davis, HL and McCluskie, MJ (2013) Selection of a novel anti-nicotine vaccine: influence of antigen design on antibody function in mice. PLoS One, 8 (10). e76557-?.

Hansen, SU, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Cole, C, Rushton, G, Avizienyte, E, Jayson, GC and Gardiner, JM (2013) Tetrasaccharide iteration synthesis of a heparin-like dodecasaccharide and radiolabelling for in vivo tissue distribution studies. Nature Communications, 4 (1).

Takemoto, N, Suehara, T, Frisco, HL, Sato, S-I, Sezaki, T, Kusamori, K, Kawazoe, Y, Park, SM, Yamazoe, S, Mizuhata, Y, Inoue, R, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Hansen, SU, Jayson, GC, Gardiner, JM, Kanaya, T, Tokitoh, N, Ueda, K, Takakura, Y, Kioka, N, Nishikawa, M and Uesugi, M (2013) Small-Molecule-Induced Clustering of Heparan Sulfate Promotes Cell Adhesion. Journal Of The American Chemical Society, 135 (30). 11032 -11039.

Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Hansen, SU, Avizienyte, E, Rushton, G, Cole, C, Jayson, GC and Gardiner, JM (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.

Hansen, SU, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Jayson, GC and Gardiner, JM (2013) First Gram-Scale Synthesis of a Heparin-Related Dodecasaccharide. Organic Letters, 15 (1). 88 - 91.

Hansen, SU, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Barath, M, Broberg, KR, Avizienyte, E, Helliwell, M, Raftery, J, Jayson, GC and Gardiner, JM (2012) Synthesis and Scalable Conversion of l-Iduronamides to Heparin-Related Di- and Tetrasaccharides. Journal Of Organic Chemistry, 77 (18). 7823 -7843.

Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Gardiner, JM (2011) A synthesis of C-glycosidic multivalent mannosides suitable for divergent functionalized conjugation. Tetrahedron Letters, 52 (25). 3216 - 3218.

Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 and Gardiner, JM (2010) Adaptable Synthesis of C-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization. Organic Letters, 12 (22). 5262 - 5265.

Florence, GJ, Aslam, T, Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306, Milne, GDS and Conway, SJ (2009) Thieme Chemistry Journal Awardees - Where are They Now? Synthesis of the Marine Glycolipid Dioctadecanoyl Discoside. Synlett, 19. 3099 -3102.

Conway, SJ and Miller, GJ ORCID: https://orcid.org/0000-0001-6533-3306 (2007) Biology-enabling inositol phosphates, phosphatidylinositol phosphates and derivatives. Natural Product Reports, 24 (4). 687 - 707.