Premium
Synthesis and Immunological Screening of β‐Linked Mono‐ and Divalent Mannosides
Author(s) -
Mukherjee Chinmoy,
Ranta Kaarina,
Savolainen Johannes,
Leino Reko
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200041
Subject(s) - chemistry , glycosylation , propargyl , divalent , glycoside , candida albicans , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , catalysis , biology , genetics
Three different β‐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 β‐mannosylation methodology was applied to the construction of the β‐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.