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- Nilsson, Ulf, et al.
(författare)
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Synthesis, conformational analysis and comparative protein binding of a galabioside and its thioglycoside analogues
- 1996
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Ingår i: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 2:3, s. 295-302
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Tidskriftsartikel (refereegranskat)abstract
- The two thio analogues (2 and 3) of TMSEt galabioside [2-(trimethylsilyl) ethyl 4-O-(α-D-galactopyranosyl)-β-D-galactopyranoside, 1], having anomeric sulfur instead of anomeric oxygen atoms, were synthesized and their conformations investigated by NMR and computational (MM3) methods. A spacer galabioside was covalently coupled to aminated microtiter plates, and binding of a bacterial pilus adhesin (PapG) to the plates was inhibited by the soluble ligands 1, 2 and 3. The ligand 2, which has an intersaccharidic sulfur linkage, was a much less efficient inhibitor than 1, which has the natural oxygen linkage. The inhibitory power of ligand 3 was only slightly less than that of 1. An NMR experiment with 1 and 2, in which hydroxyl-group hydrogens had been partially (50%) substituted by deuterium, demonstrated the presence (in 1) and absence (in 2) of an intramolecular (HO2′-HO6) hydrogen bond. This result indicates that the conformations of 1 and 2 are different and that the difference is sufficient to cause the observed (≈30 times) reduction of the saccharide-protein binding strength.
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