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  • 1.
    Cumpstey, Ian
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ramstadius, Clinton
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Akhtar, Tashfeen
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    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 lectins2010Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 10, s. 1951-1970Artikkel i tidsskrift (Fagfellevurdert)
    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

  • 2.
    Cumpstey, Ian
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ramstadius, Clinton
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Borbas, Katalin Eszter
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Alonzi, Dominic
    Oxford University.
    Butters, Terry
    Oxford University.
    Coupling reactions of valienol C-1 electrophiles for valienamine pseudodisaccharide synthesis: synthesis and α-Glucosidase II inhibitory activity of pseudodisaccharides relevant to N-glycan biosynthesisManuskript (preprint) (Annet vitenskapelig)
  • 3.
    Ramstadius, Clinton
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Synthesis of Biologically Active Carbohydrate Mimics - Carbasugars and Pseudodisaccharides2009Licentiatavhandling, med artikler (Annet vitenskapelig)
  • 4.
    Ramstadius, Clinton
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Synthesis of Carbohydrate Mimics and Development of a Carbohydrate Epimerisation Method2010Doktoravhandling, med artikler (Annet vitenskapelig)
    Abstract [en]

    In this thesis the synthesis of several hydrolytically stable carbohydrate mimics with the potential to function as glycosidase or lectin inhibitors are described. This work is presented in Chapters 2-5.

    Chapters 2 and 3 describe synthetic efforts for producing carbasugars, and include the first synthesis of 1,2-bis-epi-valienamine and the preparation of two previously known aminocarbasugars. All three compounds were synthesised starting from D-mannose, using ring-closing metathesis as the key step. 1,2-Bis-epi-valienamine was found to inhibit Cellulomonas fimi β-mannosidase with a Ki value of 140 mM. Also included is the development of a novel synthetic route from cheap D-fructose to three mannose-mimicking carbasugars using a ring-closing metathesis strategy. Two of the compounds are potential inhibitors of the FimH adhesin.

    In Chapters 4 and 5 the synthesis of a number of pseudodisaccharides are presented; valienamine- and epi-valienamine-containing pseudodisaccharides and a small library of S-linked pseudodisaccharides were prepared. Various synthetic strategies were explored, including an alkylation strategy, Mitsunobu couplings, and sulfonate displacements. This is the first report on the synthesis of a valienamine pseudodisaccharide with β-lyxo-configuration. Two of the S-linked pseudodisaccharides were found to bind to Concanavalin A with high affinity.

    The final chapter (Chapter 6) of this thesis focuses on the development of a carbohydrate epimerisation method using transition metal catalysis. Two equilibrium constants involving gluco/manno- and gluco/allo-alcohols were determined via this method.

  • 5.
    Ramstadius, Clinton
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Boklund, Mikael
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Cumpstey, Ian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Conversion of fructose into a building block for the synthesis of carbocyclic mannose mimicsManuskript (preprint) (Annet vitenskapelig)
  • 6.
    Ramstadius, Clinton
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hekmat, Omid
    Department of Biochemistry, Lund University.
    Eriksson, Lars
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi, Avdelningen för strukturkemi.
    Stålbrand, Henrik
    Department of Biochemistry, Lund University.
    Cumpstey, Ian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    β-Mannosidase and β-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from D-mannose2009Inngår i: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 20, nr 6-8, s. 795-807Artikkel i tidsskrift (Fagfellevurdert)
    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.

  • 7.
    Ramstadius, Clinton
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Träff, Annika
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Krumlinde, Patrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäcklund, Jan-Erling
    Cumpstey, Ian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Experimental determination of the relative stability of hexopyranoside derivativesManuskript (preprint) (Annet vitenskapelig)
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