文献类型：期刊文献

英文题名：Fluoro-substitution effects in deoxyfluoro-D-glucose derivatives: random conformational search and quantum chemical calculation

作者：Zhou, Jin-Ming[1]; Zhou, Jun-Hong[2]; Zhang, Hua-Bei[3]; Dong, Xi-Cheng[1]; Chen, Min-Bo[1]

机构：[1]Chinese Acad Sci, Shanghai Inst Organ Chem, Dept Comp Chem & Cheminformat, Shanghai 200032, Peoples R China;[2]E China Univ Sci & Technol, Chem & Pharmaceut Inst, Shanghai 200237, Peoples R China;[3]Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China

年份：2006

卷号：341

期号：13

起止页码：2224

外文期刊名：CARBOHYDRATE RESEARCH

收录：;EI(收录号：20063010027792);WOS:【SCI-EXPANDED(收录号:WOS:000239753500006)】；

语种：英文

外文关键词：fluoro-substitution; fluorodeoxyglucoses; low energy conformer; random conformational search; B3LYP

摘要：The effect of substitution by the fluorine atom at different positions Of D-glucose was investigated by quantum chemical calculation of the low-energy conformers. These were obtained through the Random conformational search method. The geometries of conformers were optimized at the RHF/6-31 (d) level, then reoptimization and vibrational analysis were performed at the B3LYP/6-31+G(d) level. Single-point energies were calculated at the B3LYP/6-311++G(2d,2p) level. The free energies of solvation in water were calculated utilizing the AM1-SM5.4 solvation model. For all substitution positions, the ring conformation does not change much, and the pyranoid C-4(1) conformers are dominant, while variations in the substitution site result in different effects in the network of hydrogen bonds, anomeric effect, the solvation free energy, and the ratio of alpha- and beta-anomers. (c) 2006 Elsevier Ltd. All rights reserved.