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

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Monika Poláková, Mattias U. Roslund, Filip S. Ekholm, Tiina Saloranta, and Reko Leino
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2009
Journal: European Journal of Organic Chemistry
Journal acronym: EUR J ORG CHEM
Issue number: 6
Start page: 870
End page: 888
Number of pages: 19
ISSN: 1434-193X


Abstract

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)


Keywords

Asymmetric synthesis, Glycosylation, NMR spectroscopy, Oligosaccharides

Last updated on 2019-22-09 at 02:39