O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside.
Cast your vote
You can rate an item by clicking the amount of stars they wish to award to this item.
When enough users have cast their vote on this item, the average rating will also be shown.
Your vote was cast
Thank you for your feedback
Thank you for your feedback
MetadataShow full item record
AbstractSelenoglycosides 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.
CitationO-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside. 2016, 12:2828-2833 Beilstein J Org Chem
AffiliationHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS),Saarland Universitätscampus E8.1, 66123 Saarbrücken, Germany.
The following license files are associated with this item:
Except where otherwise noted, this item's license is described as http://creativecommons.org/licenses/by-nc-sa/4.0/
- Crystal Structures of Fungal Tectonin in Complex with O-Methylated Glycans Suggest Key Role in Innate Immune Defense.
- Authors: Sommer R, Makshakova ON, Wohlschlager T, Hutin S, Marsh M, Titz A, Künzler M, Varrot A
- Issue date: 2018 Mar 6
- Combinatorial synthesis of an oligosaccharide library by using beta-bromoglycoside-mediated iterative glycosylation of selenoglycosides: rapid expansion of molecular diversity with simple building blocks.
- Authors: Yamago S, Yamada T, Ito H, Hara O, Mino Y, Yoshida J
- Issue date: 2005 Oct 21
- Structures of the glycopeptidolipid antigens of serovars 25 and 26 of the Mycobacterium avium serocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins.
- Authors: Aspinall GO, Gammon DW, Sood RK, Chatterjee D, Rivoire B, Brennan PJ
- Issue date: 1992 Dec 31
- Synthesis of the methyl thioglycosides of 2-, 3-, and 4-deoxy-L-fucose.
- Authors: Hasegawa A, Ando T, Kato M, Ishida H, Kiso M
- Issue date: 1994 Apr 16
- Synthesis of di-O-glycosyl derivatives of methyl alpha-L-rhamnopyranoside.
- Authors: Nifant'ev NE, Lipkind GM, Shashkov AS, Kochetkov NK
- Issue date: 1992 Jan