Several transition states from C1 to skew conformations of β-d-glucopyranose |
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Authors: | Youji Kurihara Kazuyoshi Ueda |
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Institution: | aDepartment of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-Ku, Yokohama 240-8501, Japan |
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Abstract: | The interconversion pathways in the ring distortion of β-d-glucopyranose were investigated using density functional calculations. We examined the energies of several conformers of β-d-glucopyranose and tried to obtain the transition-state conformation and determine the pathway between a 4C1 chair and some distorted ring conformers. The results showed that two E3/2H3 conformations and one E3/4H3 conformation were transition states in such ring puckering. The transition state with the lowest energy conformation is the E3/2H3 ring conformation with the side-chain conformation of r-ggG+. Intrinsic reaction coordinate calculations indicated that the E3/2H3 conformation with the lowest conformational energy is a transition state of the ring interconversion path between the conformations of 4C1 and 2SO/B3,O. The energy barrier of this interconversion was 6.13 kcal/mol. As far as we know, this is the first example of finding pathways for an interconversion of glucopyranose ring puckering at the level of a quantum chemical calculation. |
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Keywords: | Glucopyranose conformation Density functional calculation Transition state Ring puckering |
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