Synthesis of beta-(1 -> 2)-Linked Oligomannosides

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Publikationens författare: Monika Poláková, Mattias U. Roslund, Filip S. Ekholm, Tiina Saloranta, and Reko Leino
Förläggare: WILEY-V C H VERLAG GMBH
Publiceringsår: 2009
Tidskrift: European Journal of Organic Chemistry
Tidskriftsakronym: EUR J ORG CHEM
Nummer: 6
Artikelns första sida, sidnummer: 870
Artikelns sista sida, sidnummer: 888
Antal sidor: 19
ISSN: 1434-193X


Abstrakt

b-(1 -> 2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of beta-(1 -> 2)-linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected beta-(1 -> 2)-linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)


Nyckelord

Asymmetric synthesis, Glycosylation, NMR spectroscopy, Oligosaccharides

Senast uppdaterad 2020-22-02 vid 06:50