- AN ANTIMICROBIAL AGENT
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The present invention relates to novel thioglycosides of D-galactofuranose that have an antimicrobial action, methods for their synthesis, pharmaceutical compositions containing them and methods for the treatment of patients suffering microbial infection.
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Page/Page column 21
(2010/02/07)
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- Studies of UDP-galactopyranose mutase from Escherichia coli: An unusual role of reduced FAD in its catalysis
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The galactofuranose moiety found in many surface constituents of microorganisms is derived from UDP-D-galactopyranose (UDP-Galp) via a unique ring contraction reaction catalyzed by UDP-Galp mutase. This enzyme, which has been isolated from several bacteri
- Zhang, Qibo,Liu, Hung-Wen
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p. 9065 - 9070
(2007/10/03)
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- One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi
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Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O- benzoyl-2-deoxy-α-D-glucopyranoside (4) with penta-O-benzoyl-β-D- galactopyranose (6) gave the derivative of β-D-Galp-(1 → 6)-α-D-GlcNAc 7 in 80% yield. This was glycosylated with penta-O-benzoyl-α,β-D- galactofuranose (5), employing the same catalyst, to afford the protected benzyl per-O-benzoyl-β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]D-GlcNAc 10 in 41% yield. Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). β-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide β-D-Galf(1 → 4)[ β-D-Galp(l → 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi.
- Gallo-Rodriguez, Carola,Varela, Oscar,De Lederkremer, Rosa M.
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p. 163 - 170
(2007/10/03)
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- A convenient iodonium-ion-assisted synthesis of an immunologically active tetrameric β(1->5)-linked D-galactofuranoside from the extracellular polysaccharide of Aspergillus and Penicillium species
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The non-terminal glycosyl donor, ethyl 2,3-di-O-benzoyl-5-O-(chloroacetyl)-6-O-pivaloyl-1-thio-α-D-galactofuranoside, could be used, with the promotor N-iodosuccinimide and catalytic trifluoromethanesulfonic acid, for the preparation of β-D-galf-(1->5)-β-
- Zuurmond, H. M.,Klein, P. A. M. van der,Veeneman, G. H.,Boom, J. H. van
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p. 437 - 441
(2007/10/02)
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