O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside.

2.50
Hdl Handle:
http://hdl.handle.net/10033/620805
Title:
O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside.
Authors:
Sommer, Roman; Hauck, Dirk; Varrot, Annabelle; Imberty, Anne; Künzler, Markus; Titz, Alexander ( 0000-0001-7408-5084 )
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.
Affiliation:
Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS),Saarland Universitätscampus E8.1, 66123 Saarbrücken, Germany.
Citation:
O-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
Journal:
Beilstein journal of organic chemistry
Issue Date:
2016
URI:
http://hdl.handle.net/10033/620805
DOI:
10.3762/bjoc.12.282
PubMed ID:
28144356
Type:
Article
Language:
en
Appears in Collections:
publications of the junior research group chemical biology of carbohydrates ([HIPS]CBCH)

Full metadata record

DC FieldValue Language
dc.contributor.authorSommer, Romanen
dc.contributor.authorHauck, Dirken
dc.contributor.authorVarrot, Annabelleen
dc.contributor.authorImberty, Anneen
dc.contributor.authorKünzler, Markusen
dc.contributor.authorTitz, Alexanderen
dc.date.accessioned2017-02-03T11:38:00Z-
dc.date.available2017-02-03T11:38:00Z-
dc.date.issued2016-
dc.identifier.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 Chemen
dc.identifier.pmid28144356-
dc.identifier.doi10.3762/bjoc.12.282-
dc.identifier.urihttp://hdl.handle.net/10033/620805-
dc.description.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.en
dc.language.isoenen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.titleO-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside.en
dc.typeArticleen
dc.contributor.departmentHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS),Saarland Universitätscampus E8.1, 66123 Saarbrücken, Germany.en
dc.identifier.journalBeilstein journal of organic chemistryen

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