- The synthesis and biological evaluation of mycobacterial p-hydroxybenzoic acid derivatives (p-HBADs)
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Mycobacterium tuberculosis establishes chronic infection and causes disease through manipulation of the host's innate and adaptive immune response. The bacterial cell wall is highly complex and contains a rich variety of glycosylated compounds that are se
- Bourke, Jean,Brereton, Corinna F.,Gordon, Stephen V.,Lavelle, Ed C.,Scanlan, Eoin M.
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p. 1114 - 1123
(2014/02/14)
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- Synthesis of the α-D-GlcpA-(1 → 3)-α-L-Rhap-(1 → 2)-L-Rha trisaccharide isolated from the cell wall hydrolyzate of the green alga, Chlorella vulgaris
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The title trisaccharide was synthesized from 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride (10), ethyl 2,4-di-O-benzyl-1-thio- (5) and benzyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (9). The disaccharide 11 obtained from compounds 5 and 10 was used as the glycosyl donor to glycosylate the rhamnopyranoside derivative 9 having free OH-2 using the NIS-AgOTf-mediated glycosylation methodology. Zemplen deacetylation of the trisaccharide 12 resulted in the 6″-OH derivative (13), which was selectively oxidized with CrO3 to the uronic acid derivative 14. The benzyl groups were removed by catalytic hydrogenolysis to furnish the target trisaccharide (1).
- Sajtos, Ferenc,Hajko, Janos,Koever, Katalin E,Liptak, Andras
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p. 253 - 259
(2007/10/03)
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- Chemical synthesis of the pyruvic acetal-containing trisaccharide unit of the species-specific glycopeptidolipid from Mycobacterium avium serovariant 8
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The functionalized, pyruvic acetal-containing haptenic trisaccharide, p- trifluoroacetamidophenyl 6-deoxy-2-O-[3-O-[4,6-O-(S)-(1- methoxycarbonylethylidene)-3-O-methyl-β-D-glucopyranosyl]-α-L- rhamnopyranosyl)-α-L-talopyranoside (19), a component of the g
- Bajza,Kerekgyarto,Hajko,Szilagyi,Liptak
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p. 111 - 120
(2007/10/02)
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