Synthetic studies towards sphingosine-related metabolites

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en
dc.contributor.author Brunner, Martin
dc.date.accessioned 2012-02-17T07:31:54Z
dc.date.available 2012-02-17T07:31:54Z
dc.date.issued 2006-02-11
dc.identifier.isbn 951-22-8019-1
dc.identifier.issn 1236-2999
dc.identifier.uri https://aaltodoc.aalto.fi/handle/123456789/2668
dc.description.abstract Metabolites of the thermophilic fungi Myriococcum albomyces and Mycelia sterilia such as myriocin (thermozymocidin, ISP-1), the mycestericins and the sphingofungins structurally resemble the sphingosines, important components of cell membranes. The close relation of the metabolites to the sphingosines suggests an important role in regulatory processes of eukaryotic cell membranes. All the compounds revealed in vitro remarkable immunosuppressive activity and their pharmaceutical potential has led to the development of promising novel immunosuppressants. The derivative FTY720 is the first S1P receptor agonist and has a different mode of action than the commonly used calcineurin-inhibitors CsA (Neoral®) and FK506 (Prograf®), or the macrolides RAD (Certican™) and rapamycin. FTY720 is currently in clinical phase III trials for therapeutic use in the areas of transplantation and autoimmunity and was recently found to be effective in kidney transplantation in humans. Studies on the sphingosines and Garner's aldehyde have prompted us to investigate sphingosine-related metabolites such as myriocin, the mycestericins, or the sphingofungins. Many of these metabolites bear an α-substituted serine moiety as a common feature, and the formation of this quaternary centre represents the main synthetic challenge in total syntheses of these metabolites. The task of this thesis is to establish a synthetic route for the controlled, stereoselective formation of the quaternary carbon centre of α-substituted serine derivatives, with the option of choice of the absolute configuration. An efficient and stereoselective method for this is based on the principle of self-regeneration of stereocentres (SRS). en
dc.format.extent 52, [app]
dc.format.mimetype application/pdf
dc.language.iso en en
dc.publisher Helsinki University of Technology en
dc.publisher Teknillinen korkeakoulu fi
dc.relation.ispartofseries Organic chemistry report en
dc.relation.ispartofseries 1/2006 en
dc.relation.haspart M. Brunner, T. Straub, P. Saarenketo, K. Rissanen, and A. M. P. Koskinen. 2004. Highly diastereoselective methylation of five-ring N,O-acetals. Letters in Organic Chemistry 1, number 3, pages 268-270. [article1.pdf] © 2004 Bentham Science Publishers. By permission.
dc.relation.haspart M. Brunner and A. M. P. Koskinen. 2004. Highly diastereoselective aldol additions to five-ring N,O-acetals. Tetrahedron Letters 45, number 15, pages 3063-3065. [article2.pdf] © 2004 Elsevier Science. By permission.
dc.relation.haspart M. Brunner, P. Saarenketo, T. Straub, K. Rissanen, and A. M. P. Koskinen. 2004. Stereocontrolled α-alkylation of fully protected L-serine. European Journal of Organic Chemistry 2004, number 18, pages 3879-3883.
dc.relation.haspart M. Brunner and A. M. P. Koskinen. 2004. Biology and chemistry of sphingosine-related metabolites. Current Organic Chemistry 8, number 17, pages 1629-1645. [article4.pdf] © 2004 Bentham Science Publishers. By permission.
dc.relation.haspart M. Brunner, M. Nissinen, K. Rissanen, T. Straub, and A. M. P. Koskinen. 2005. Diastereoselective formation of highly functionalised α-substituted amino acid derivatives via aldol addition. Journal of Molecular Structure 734, numbers 1-3, pages 177-182. [article5.pdf] © 2005 Elsevier Science. By permission.
dc.subject.other Biotechnology en
dc.title Synthetic studies towards sphingosine-related metabolites en
dc.type G5 Artikkeliväitöskirja fi
dc.description.version reviewed en
dc.contributor.department Department of Chemical Technology en
dc.contributor.department Kemian tekniikan osasto fi
dc.subject.keyword L-serine en
dc.subject.keyword self-regeneration of stereocentres en
dc.subject.keyword asymmetric synthesis en
dc.subject.keyword diastereoselection en
dc.subject.keyword sphingolipids en
dc.subject.keyword myriocin en
dc.subject.keyword mycestericins en
dc.identifier.urn urn:nbn:fi:tkk-006554
dc.type.dcmitype text en
dc.type.ontasot Väitöskirja (artikkeli) fi
dc.type.ontasot Doctoral dissertation (article-based) en
dc.contributor.lab Laboratory of Organic Chemistry en
dc.contributor.lab Orgaanisen kemian laboratorio fi


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