Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose
- The synthesis of six analogs of N,N;-diacetylchitobiose is reported, including a novel transglycosylation reaction for the preparation of S-aryl thioglycosides. The conformations of the compounds were studied by a combination of NMR spectroscopy and molecular modeling, using force field calculations. In the case of the S-aryl thioglycosides with exclusively S-glycosidic linkages, dihedral angles of the disaccharidic S-glycosidic bonds, ;; and ;; and of the S-arylglycoside bonds, ; and ;, were found to be similar, whereas they were different in mixed glycosides and in a thiazoline derivative. An adequate correlation between the calculated H,H-distances of the local minima and the measured NOE contacts was achieved by applying population-weighted averages over participating conformers based on weighted relative energies.
Author details: | Anja FettkeGND, Dirk Peikow, Martin G. Peter, Erich KleinpeterORCiDGND |
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URL: | http://www.sciencedirect.com/science/journal/00404020 |
DOI: | https://doi.org/10.1016/j.tet.2009.03.067 |
ISSN: | 0040-4020 |
Publication type: | Article |
Language: | English |
Year of first publication: | 2009 |
Publication year: | 2009 |
Release date: | 2017/03/25 |
Source: | Tetrahedron. - ISSN 0040-4020. - 65 (2009), 22, S. 4356 - 4366 |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
Peer review: | Referiert |