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  • 1.
    Akhtar, Tashfeen
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Investigations into the synthesis of amine-linked neodisaccharides2007In: Tetrahedron Letters, ISSN 0040-4039, Vol. 48, p. 8673-8677Article in journal (Refereed)
  • 2.
    Akhtar, Tashfeen
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Department of Physical, Inorganic and Structural Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Unusual synthesis of carbohydrate sec-sec ether-linked pseudodisaccharides2008In: Carbohydrate Research, ISSN 0008-6215, Vol. 343, no 12, p. 2094-2100Article in journal (Refereed)
  • 3.
    Burkhardt, Anja
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Structural Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    (Z)-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose O-benzyloxime2009In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. E65, no Part 3, p. o633-o633Article in journal (Refereed)
  • 4. Cribiù, Riccardo
    et al.
    Borbas, K. Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    On the synthesis of vinyl and phenyl C-furanosides by stereospecific debenzylative cycloetherification2009In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 65, no 10, p. 2022-2031Article in journal (Refereed)
  • 5.
    Cribiù, Riccardo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides2008In: Chemical Communications, ISSN 1359-7345, no 10, p. 1246-1248Article in journal (Refereed)
  • 6.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Intramolecular aglycon delivery2008In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 343, no 10-11, p. 1553-1573Article, review/survey (Other academic)
  • 7.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    New oligosaccharide analogues: non-glycosidically linked thioether-bridged pseudodisaccharides2006In: Synlett, ISSN 0936-5214, no 11, p. 1711-1714Article in journal (Refereed)
  • 8.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Short synthesis of a benzyl ether protected building block for the synthesis of carbocyclic galactopyranose mimics2010In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 345, no 8, p. 1056-1060Article in journal (Refereed)
  • 9.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides2009In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 344, no 17, p. 2285-2310Article, review/survey (Refereed)
  • 10.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Alonzi, Dominic S.
    Butters, Terry D.
    Carbasugar-thioether pseudodisaccharides related to N-glycan biosynthesis2009In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 344, no 4, p. 454-459Article in journal (Refereed)
  • 11.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Department of Physical, Inorganic and Structural Chemistry.
    Bis(methyl 2,4,6-tri-O-acetyl-beta-D-allofuranosid-3-yl)sulfane2007In: Acta Crystallographica Section E, ISSN 1600-5368, Vol. E63, p. o4197-Article in journal (Refereed)
  • 12.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gehrke, Sebastian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Erfan, Sayeh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cribiù, Riccardo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Studies on the synthesis of valienamine and 1-epi-valienamine starting from D-glucose or L-sorbose2008In: Carbohydrate Research, ISSN 0008-6215, Vol. 343, no 10-11, p. 1675-1692Article in journal (Refereed)
  • 13.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ramstadius, Clinton
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Akhtar, Tashfeen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Goldstein, Irwin J
    Department of Biological Chemistry, University of Michigan Medical School, Ann Arbor, MI .
    Winter, Harry C
    Department of Biological Chemistry, University of Michigan Medical School, Ann Arbor, MI .
    Non-glycosidically linked pseudodisaccharides: thioethers, sulfoxides, sulfones, ethers, selenoethers, and their binding to lectins2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 10, p. 1951-1970Article in journal (Refereed)
    Abstract [en]

    Hydrolytically stable non-glycosidically linked tail-to-tail pseudodisaccharides are linked by a single bridging atom remote from the anomeric centre of the constituent monosaccharides. Some such pseudodisaccharides with sulfur or oxygen bridges were found to act as disaccharide mimetics in their binding to the Banana Lectin and to Concanavalin A. A versatile synthetic route to a small library of such compounds is described

  • 14.
    Fournière, Viviane
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of non-glycosidically linked selenoether pseudodisaccharides2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 16, p. 2127-2129Article in journal (Refereed)
    Abstract [en]

    Non-glycosidically linked disaccharide mimetics with a selenoether functionality linking the two monosaccharide residues have been synthesised. Protected Glc(Se3–3)Glc, Glc(Se3–6)Glc and Glc(Se3–6)Man structures were obtained. Selenium was introduced by displacement of carbohydrate sulfonates with a selenobenzoate anion. Conversion into diselenides by methanolysis of the benzoate and aerial oxidation was followed by reduction of the diselenides to selenolates, and in situ displacement of a second carbohydrate sulfonate in an SN2 reaction to give selenoethers. Glc(Se3–3)Glc and Glc(Se3–6)Glc were also obtained in deprotected form.

  • 15.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    First synthesis of 4a-carba-beta-D-galactofuranose2007In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 48, no 52, p. 9073-9076Article in journal (Refereed)
  • 16.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of carbadisaccharide mimics of galactofuranosides2009In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 50, no 36, p. 5142-5144Article in journal (Refereed)
  • 17.
    Ramstadius, Clinton
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hekmat, Omid
    Department of Biochemistry, Lund University.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Stålbrand, Henrik
    Department of Biochemistry, Lund University.
    Cumpstey, Ian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    β-Mannosidase and β-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from D-mannose2009In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 20, no 6-8, p. 795-807Article in journal (Refereed)
    Abstract [en]

    A partially protected C-5C-5a unsaturated carbasugar with α-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with β-lyxo (i.e., corresponding to β-manno at C-1–C-4), α-lyxo (i.e., corresponding to α-manno at C-1–C-4) and β-2-acetamido-2-deoxy-xylo (i.e., corresponding to β-GlcNAc at C-1–C-4) configurations. This is the first report of the synthesis of the β-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi β-mannosidase (CfMan2A) with Ki 140 μM. We report the crystal structures of three protected C-5C-5a unsaturated carbasugars with lyxo configuration.

1 - 17 of 17
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