O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside
Abstract
Selenoglycosides are used as reactive glycosyl donors in the syntheses of oligosaccharides. In addition, such heavy atom analogs of natural glycosides are useful tools for structure determination of their lectin receptors using X-ray crystallography. Some lectins, e.g., members of the tectonin family, only bind to carbohydrate epitopes with O-alkylated ring hydroxy groups. In this context, we report the first synthesis of an O-methylated selenoglycoside, specifically methyl 2-O-methyl-L-selenofucopyranoside, a ligand of the lectin tectonin-2 from the mushroom Laccaria bicolor. The synthetic route required a strategic revision and further optimization due to the intrinsic lability of alkyl selenoglycosides, in particular for the labile fucose. Here, we describe a successful synthetic access to methyl 2-O-methyl-L-selenofucopyranoside in 9 linear steps and 26% overall yield starting from allyl L-fucopyranoside. Show more
Permanent link
https://doi.org/10.3929/ethz-b-000128282Publication status
publishedExternal links
Journal / series
Beilstein Journal of Organic ChemistryVolume
Pages / Article No.
Publisher
Beilstein-Institut zur Förderung der Chemischen WissenschaftenSubject
Carbohydrate chemistry; Fucose; Lectin; Selenoglycoside; escherichia-coliOrganisational unit
03408 - Aebi, Markus (emeritus) / Aebi, Markus (emeritus)
More
Show all metadata