Conformational analysis of the anomeric forms of kojibiose, nigerose, and maltose using MM3 |
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Authors: | Michael K Dowd Jing Zeng Alfred D French Peter J Reilly |
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Institution: | a Department of Chemical Engineering, Iowa State University, Ames, Iowa 50011 U.S.A. b Southern Regional Research Center, U.S. Department of Agriculture, New Orleans, Louisiana 70179 USA |
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Abstract: | Energy surfaces were computed for relative orientations of the relaxed pyranosyl rings of the two anomeric forms of kojibiose, nigerose, and maltose, the (1 → 2)- , (1 → 3)- - and (1 → 4)- -linked
-glucosyl disaccharides, respectively. Twenty-four combinations of starting conformations of the rotatable side-groups were considered for each disaccharide. Optimized structures were calculated using MM3 on a 20° grid spacing of the torsional angles about the glycosidic bonds. The energy surfaces of the six disaccharides were similar in many respects but differed in detail within the low-energy regions. The maps also illustrate the importance of the exo-anomeric effect and linkage type in determining the conformational flexibility of disaccharides. Torsional conformations of known crystal structures of maltosyl-containing molecules lie in a lower MM3 energy range than previously reported. |
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