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All › Heterocyclic Compounds › Alkaloids › Swainsonine

Swainsonine (0)

      Articles on Swainsonine

      1. Synthesis of (-)-swainsonine and (-)-8-epi-swainsonine by the addition of allenylmetals to chiral α,β-alkoxy sulfinylimines.
        Julien J Louvel, Fabrice F Chemla, ... Alejandro A Pérez-Luna

        Org Lett 13(24):6452-5 (2011) PMID 22082237

        The asymmetric synthesis of (-)-swainsonine and (-)-8-epi-swainsonine is reported through the addition of either the allenylzinc or the allenyl lithio cyanocuprate reagents derived from [3-(methoxymethoxy)prop-1-ynyl]trimethylsilane to enantiopure α,β-dialkoxy N-tert-butanesulfinyl...
      2. N-glycan-defective breast cancer cells induce a phenotypic switch in polarization of bone marrow-derived macrophages.
        Haidan Chen, Huili Cai, ... Dongqing Li

        Clin Invest Med 34(2):E71-81 (2011) PMID 21463547

        To investigate the effect of N-glycan-defective mammary adenocarcinoma cells on the polarization of macrophages. N-glycan-defective breast cancer cells (MA782 cells) were prepared by swainsonine (SW) treatment and the cytotoxicity of SW to MA782 cells was evaluated us...
      3. Swainsonine-producing fungal endophytes from major locoweed species in China
        Yongtao Yu, Qingmei Zhao, ... Qinfan Li

        Toxicon 56(3):9 (2010) PMID 20380845

        Locoweeds including the toxic species of Astragalus spp and Oxytropis spp. are widely distributed in the western region of China and result in a chronic neurological disease known as locoism in animals. To determine the presence of swainsonine-producing fungal endophyte of major locoweed species in...
      4. Development of a transformation system in the swainsonine producing, slow growing endophytic fungus, Undifilum oxytropis
        Suman Mukherjee, Angus L Dawe, and Rebecca Creamer

        J Microbiol Methods 81(2):6 (2010) PMID 20211666

        We report the development of protoplast and transformation system for U. oxytropis. Fungal mycelia required for generating protoplasts were grown in liquid culture, then harvested and processed with various enzymes. Protoplasts were transformed with a fungal specific vector driving the expression of...
      5. Structural investigation of the binding of 5-substituted swainsonine analogues to Golgi alpha-mannosidase II.
        Douglas A Kuntz, Shinichi Nakayama, ... David R Rose

        Chembiochem 11(5):673-80 (2010) PMID 20209559

        We characterize the binding of 5alpha-substituted swainsonine analogues to the soluble catalytic domain of Drosophila GMII by X-ray crystallography. These inhibitors enjoy an advantage over previously reported GMII inhibitors in that they did not significantly decrease the inhibitory potential of th...
      6. Studies toward new anti-cancer strategies based on alpha-mannosidase inhibition.
        Sandrine Gerber-Lemaire and Lucienne Juillerat-Jeanneret

        Chimia (Aarau) 64(9):634-9 (2010) PMID 21138109

        Changes in the glycosylation pattern of cellular glycoproteins constitute a hallmark in human cancer and influence tumor progression, suggesting that inhibitors of selected glycosidases may control cancer progression. Following the studies on swainsonine, a natural inhibitor of Golgi alpha-mannosida...
      7. A formal synthesis of swainsonine by gold-catalyzed allene cyclization.
        Roderick W RW Bates and Mark R MR Dewey

        Org Lett 11(16):3706-8 (2009) PMID 19719203

        A formal synthesis of swainsonine has been achieved using a highly efficient and diastereoselective gold(III)-catalyzed allene cyclization.
      8. Binding of sulfonium-ion analogues of di-epi-swainsonine and 8-epi-lentiginosine to Drosophila Golgi alpha-mannosidase II: the role of water...
        Nag S NS Kumar, Douglas A DA Kuntz, ... David R DR Rose

        Proteins 71(3):1484-96 (2008) PMID 18076078

        Retaining glycosidases operate by a two-step catalytic mechanism in which the transition states are characterized by buildup of a partial positive charge at the anomeric center. Sulfonium-ion analogues of the naturally occurring glycosidase inhibitors, swainsonine and 8-epi-lentiginosine, in which t...
      9. De novo asymmetric synthesis of 8a-epi-swainsonine.
        Jason N Abrams, Ravula Satheesh Babu, ... George A O'Doherty

        J Org Chem 73(5):1935-40 (2008) PMID 18237188

        An enantioselective and diastereocontrolled approach to 8a-epi-d-swainsonine has been developed from achiral furfural. The key step to this synthesis was a one-pot procedure for the hydrogenolytic removal of two protecting groups and two intramolecular reductive amination reactions. The absolute ste...
      10. Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-h...
        K S KS Ajish Kumar, Vinod D VD Chaudhari, and Dilip D DD Dhavale

        Org Biomol Chem 6(4):703-11 (2008) PMID 18264570

        The utility of a D-glucose-derived aziridine carboxylate was demonstrated for the synthesis of polyhydroxylated quinolizidine and indolizidine alkaloids. The chemoselective reduction of 1 followed by two-carbon homologation by the Wittig reaction afforded gamma,delta-aziridino-alpha,beta-unsaturated...