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Synthesis, conformational analysis and comparative protein binding of a galabioside and its thioglycoside analogues

Nilsson, Ulf LU ; Johansson, Roger LU and Magnusson, Göran LU (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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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}},
}