Synthesis and Immunological Screening of beta-Linked Mono- and Divalent Mannosides

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Mukherjee C, Ranta K, Savolainen J, Leino R
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2012
Journal: European Journal of Organic Chemistry
Journal acronym: EUR J ORG CHEM
Issue number: 15
Start page: 2957
End page: 2968
Number of pages: 12
ISSN: 1434-193X


Abstract

Three different beta-linked divalent mannosides, along with their corresponding monovalent counterparts, have been designed and chemically synthesized by coupling the corresponding propargyl (propargyl alcohol in the case of the monovalent compounds) and 2-azidoethyl glycosides by using an efficient click chemistry protocol. Crich's beta-mannosylation methodology was applied to the construction of the beta-mannosidic linkages. All the glycosylation reactions gave moderate-to-good yields with high selectivities. A competitive inhibition enzyme-linked immunosorbent assay (ELISA) was performed to determine the inhibition, by the synthesized mannosides, of specific human IgG binding to low-molecular-weight Candida albicans mannan; moderate inhibition capacity was observed for some of the compounds.


Keywords

Biological activity, Click chemistry, Glycosylation, Medicinal chemistry

Last updated on 2019-19-09 at 05:49