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  • 1. 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)
  • 2.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Agrawal, Santosh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Borbas, K. Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iridium-catalysed condensation of alcohols and amines as a method for aminosugar synthesis2011In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 47, no 27, p. 7827-7829Article in journal (Refereed)
    Abstract [en]

    Primary carbohydrate amines at primary and secondary carbons are alkylated by alcohols in the presence of [Cp*IrCl2]2. When primary carbohydrate alcohols are used as the coupling partners and in the presence of Cs2CO3, amine-linked pseudodisaccharides are obtained. Secondary carbohydrate alcohols are unaffected under these conditions, which allows regioselective reactions.

  • 3.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ramstadius, Clinton
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Borbas, K. Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Investigation of Coupling Reactions for the Synthesis of Valienamine Pseudodisaccharides2011In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 12, p. 1701-1704Article in journal (Refereed)
    Abstract [en]

    Amine-linked pseudodisaccharides based on valienamine were synthesised by C-N bond-forming reactions between valienol-derived C-1 electrophiles and carbohydrate nitrogen nucleophiles. Palladium-catalysed coupling with trichloroacetimidate leaving groups, Mitsunobu reactions with a nosylamide nucleophile, and alkylation of amines by C-1 bromides were investigated.

  • 4.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ramstadius, Clinton
    Borbas, K. Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Alonzi, Dominic S.
    Butters, Terry D.
    Synthesis and alpha-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis2011In: Bioorganic & Medicinal Chemistry Letters, ISSN 0960-894X, E-ISSN 1090-2120, Vol. 21, no 18, p. 5219-5223Article in journal (Refereed)
    Abstract [en]

    Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for alpha-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(alpha 1 -> 3)Glc and Glc(alpha 1 -> 3) Man disaccharides representing the linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis. These (N1 -> 3)-linked pseudodisaccharides were found to have some alpha-Glucosidase II inhibitory activity, while two other (N1 -> 6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme. (C)

  • 5.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ramstadius, Clinton
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Borbas, Katalin Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    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 biosynthesisManuscript (preprint) (Other academic)
  • 6.
    Laakso, Johanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Borbas, Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Towards lanthanide-based responsive luminescent probes for the detection of reactive oxygen species2010In: Abstracts of Papers, 240th ACS National Meeting, Boston, MA, United States, August 22-26, 2010, American Chemical Society , 2010Conference paper (Other academic)
  • 7.
    Laakso, Johanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rosser, Geraldine A.
    Szijjarto, Csongor
    Beeby, Andrew
    Borbas, Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of chlorin sensitized near infrared emitting lanthanide complexes2012In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 51, no 19, p. 10366-10374Article in journal (Refereed)
    Abstract [en]

    Lanthanide (Yb3+, Nd3+) complexes equipped with red-absorbing hydroporphyrin (chlorin) antennae were synthesized and characterized. The syntheses are scalable, highly modular, and enable the introduction of different chlorins functionalized with a single reactive group (COOH or NH2). Absorption maxima were dependent on chlorin substitution pattern (monomeso aryl or dimeso aryl) and metalation state (free base or zinc chelate). The complexes benefit from dual chlorin (610-639 nm) and lanthanide (980 or 1065 nm for Yb- or Nd-complexes, respectively) emission in the biologically relevant red and near IR region of the spectrum.

  • 8. Pershagen, Elias
    et al.
    Borbas, Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Europium-based turn-on bioconjugatable luminescent probe for detecting H2O2 in live cells.2011In: Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011, 2011Conference paper (Other academic)
    Abstract [en]

    A Europium-based turn-on bioconjugatable luminescent probe for detecting hydrogen peroxide in live cells is presented.  The probe relies on a chemoselective boronate-to-phenol switch in response to hydrogen peroxide, resulting in an enhanced lanthanide sensitization.  Excitation can be performed by visible light.  Bioconjugation is achived by Cu(I) catalyzed azide-alkyne cycloaddn.

  • 9.
    Pershagen, Elias
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nordholm, Johan
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Borbas, K. Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Luminescent Lanthanide Complexes with Analyte-Triggered Antenna Formation2012In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 134, no 24, p. 9832-9835Article in journal (Refereed)
    Abstract [en]

    A new strategy for accessing analyte-responsive luminescent probes is presented. The lanthanide luminescence of Eu and Tb centers is switched on by the analyte-triggered formation of a sensitizing antenna from a nonsensitizing caged precursor. As the cage can be freely varied, an array of probes for different analytes (pd(0/2+), H2O2, F-, beta-galactosidase) can be created from the same core structure. The probe design affords nanomolar to micromolar detection limits, provides the capability to detect two analytes in parallel, and can be utilized to monitor enzymatic activity in live cells.

  • 10. Sollert, Carina
    et al.
    Borbas, Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Preparation of glycosylated pyrroles, and their use in the synthesis of analogs of the multi drug resistance-reversing natural product Tolyporphin2011In: Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011, 2011Conference paper (Other academic)
    Abstract [en]

    We present methods for the highly regio- and stereoselective synthesis of glycosylated pyrroles, and the incorporation of these compds. into larger oligopyrrolic architectures (dipyrromethanes, porphyrins, chlorins).  The flexibility of the synthesis enables the rapid generation of a wide  variety of structures.  The products are expected to be useful as synthetically accessible analogs of the biol. active natural product Tolyporphin, as well as imaging tools for biomedical applications.

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