BOKU - Universität für Bodenkultur Wien - Forschungsinformationssystem
Gewählte Publikation:
Artner, D; Stanetty, C; Mereiter, K; Zamyatina, A; Kosma, P.
(2011):
Crystal and molecular structure of methyl l-glycero-α-d-manno-heptopyranoside, and synthesis of 1⿿7 linked l-glycero-d-manno-heptobiose and its methyl α-glycoside.
Carbohydr Res. 2011; 346(13):1739-1746
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- Abstract:
- Methyl L-glycero-alpha-D-manno-heptopyranoside was synthesized in good yield by a Fischer-type glycosylation of the heptopyranose with methanol in the presence of cation-exchange resin under reflux and microwave conditions, respectively. The compound crystallized from 2-propanol in an orthorhombic lattice of space group P2(1)2(1)2 showing a comparatively porous structure with a 2-dimensional O-H center dot center dot center dot O hydrogen bond network. As model compounds for the side chain domains of the inner core structure of bacterial lipopolysaccharide, L-glycero-alpha-D-manno-heptopyranosyl-(1 -> 7)-L-glycero-D-manno-heptopyranose and the corresponding disaccharide methyl alpha-glycoside were prepared. The former compound was generated via glycosylation of a benzyl 5,6-dideoxy-hept-5-enofuranoside intermediate followed by catalytic osmylation and deprotection. The latter disaccharide was efficiently synthesized in good yield by a straightforward coupling of an acetylated N-phenyltrifluoroacetimidate heptopyranosyl donor to a methyl 2,3,4,6-tetra-O-acetyl heptopyranoside acceptor derivative followed by Zemplen deacetylation. (C) 2011 Elsevier Ltd. All rights reserved.
- Autor*innen der BOKU Wien:
- Artner Daniel
- Kosma Paul
- Stanetty Christian
- Zamyatina Alla
- Find related publications in this database (Keywords)
- Glycoside
- Lipopolysaccharide
- Heptose
- Crystal structure
- Glycosyl donor
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