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Gewählte Publikation:

Trattnig, N; Farcet, JB; Gritsch, P; Christler, A; Pantophlet, R; Kosma, P.
(2017): Synthesis of a Pentasaccharide Fragment Related to the Inner Core Region of Rhizobial and Agrobacterial Lipopolysaccharides
J ORG CHEM. 2017; 82(23): 12346-12358. FullText FullText_BOKU

Abstract:
The pentasaccharide fragment alpha-D-Man-(1 -> 5)-[alpha-D-Kdo-(2 -> 4)-)alpha-D-Kdo-(2 -> 6)-beta-D-GIcNAc-(1 -> 6)-alpha-D-G1cNAc equipped with a 3-aminopropyl spacer moiety was prepared by a sequential assembly of monosaccharide building blocks. The glucosamine disaccharide as a backbone surrogate of the bacterial lipid A region-was synthesized using an 1,3-oxazoline donor, which was followed by coupling with an isopropylidene-protected Kdo-fluoride donor to afford a protected tetrasaccharide intermediate. Eventually, an orthogonally protected manna-configured trichloroacetimidate donor was used to achieve the sterically demanding glycosylation of the 5-OH group of Kdo in good yield. The resulting pentasaccharide is suitably protected for further chain elongation at positions 3, 4, and 6 of the terminal mannose. Global deprotection afforded the target pentasaccharide to be used for the conversion into neoglycoconjugates and "clickable" ligands.
Autor/innen der BOKU Wien:
Christler Anna
Farcet Jean-Baptiste
Gritsch Philipp
Kosma Paul
Trattnig Nino
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