Lectin-bound conformations and non-covalent interactions of glycomimetic analogs of thiochitobiose
- The bound conformations of five S-glycoside analogs of N,N'-diacetylchitobiose as well as their non- covalent interactions with two lectins, Phytolacca americana lectin (PAL) and wheat germ agglutinin (WGA), are reported. The conformations of the ligands were examined by trNOESY experiments and compared with the free, solution-state conformations and molecular modeling data obtained by force field calculations. In the case of S-aryl, S-glycosides with exclusively S-glycosidic linkages, similar free and lectin-bound conformations and non-covalent interactions were found, whereas they differed for mixed glycosides and for a thiazoline derivative. In addition, STD (saturation transfer difference) NMR magnetization transfer efficiencies at three different temperatures were determined and assessed with respect to the structural differences of these pseudosaccharides. The binding epitopes of each substrate with PAL and WGA were also determined.
Author details: | Anja FettkeGND, Markus Kramer, Erich KleinpeterORCiDGND |
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URL: | http://www.sciencedirect.com/science/journal/00404020 |
DOI: | https://doi.org/10.1016/j.tet.2010.04.012 |
ISSN: | 0040-4020 |
Publication type: | Article |
Language: | English |
Year of first publication: | 2010 |
Publication year: | 2010 |
Release date: | 2017/03/25 |
Source: | Tetrahedron. - ISSN 0040-4020. - 66 (2010), 23, S. 4079 - 4088 |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
Peer review: | Referiert |