TY  - JOUR
A1  - Fettke, Anja
A1  - Peikow, Dirk
A1  - Peter, Martin G.
A1  - Kleinpeter, Erich
T1  - Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose
N2  - 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.
Y1  - 2009
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/30764
UR  - http://www.sciencedirect.com/science/journal/00404020
SN  - 0040-4020
ER  -