Synthesis, conformational analysis and comparative protein binding of a galabioside and its thioglycoside analogues
(1996) In Chemistry - A European Journal 2(3). p.295-302- 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... (More)
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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- author
- Nilsson, Ulf LU ; Johansson, Roger LU and Magnusson, Göran LU
- organization
- publishing date
- 1996
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Conformational analysis, Galabioside, Hydrogen bonds, Protein recognition, Thioglycosides
- in
- Chemistry - A European Journal
- volume
- 2
- issue
- 3
- pages
- 8 pages
- publisher
- Wiley-Blackwell
- external identifiers
-
- scopus:0000262762
- ISSN
- 0947-6539
- DOI
- 10.1002/chem.19960020310
- language
- English
- LU publication?
- yes
- id
- f63fcb9a-2137-4dff-bd01-f372c0368757
- date added to LUP
- 2023-02-07 09:18:01
- date last changed
- 2023-02-22 13:01:57
@article{f63fcb9a-2137-4dff-bd01-f372c0368757, abstract = {{<p>The two thio analogues (2 and 3) of TMSEt galabioside [2-(trimethylsilyl) ethyl 4-<i>O</i>-(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.</p>}}, author = {{Nilsson, Ulf and Johansson, Roger and Magnusson, Göran}}, issn = {{0947-6539}}, keywords = {{Conformational analysis; Galabioside; Hydrogen bonds; Protein recognition; Thioglycosides}}, language = {{eng}}, number = {{3}}, pages = {{295--302}}, publisher = {{Wiley-Blackwell}}, series = {{Chemistry - A European Journal}}, title = {{Synthesis, conformational analysis and comparative protein binding of a galabioside and its thioglycoside analogues}}, url = {{http://dx.doi.org/10.1002/chem.19960020310}}, doi = {{10.1002/chem.19960020310}}, volume = {{2}}, year = {{1996}}, }