Fluorinated and Conformationally Fixed Derivatives of L-HomoDMDP: Synthesis and Glycosidase Inhibition
文献类型：期刊论文
| 作者 | Li, Yi-Xian1; Shimada, Yousuke2; Adachi, Isao2; Kato, Atsushi2; Jia, Yue-Mei1; Fleet, George W. J.3,6; Xiao, Min4,5; Yu, Chu-Yi1,6 |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2015-05-15 |
| 卷号 | 80期号:10页码:5151-5158 |
| 英文摘要 | Fluorinated and conformationally fixed derivatives of L-homoDMDP, i.e., 2,5-dideoxy-2,5-imino-DL-glycero-L-manno-heptitol, have been synthesized from D-xylose-derived cyclic nitrone 10 with oxazolidinone 19 or 28 and oxazinanone 22 or 32 as key intermediates. An evaluation of glycosidase inhibition showed replacement of the C-6 hydroxyl groups with fluoride in L-homoDMDP and its C-6 epimer did not have a significant influence on a-glucosidase inhibition by these iminosugars, while replacement of an amino group with a cyclic carbamate group in most conformationally fixed derivatives led to a sharp decrease in the level of glycosidase inhibition, revealing the importance of the free amino group in interaction of enzymes with these molecules. |
| 收录类别 | SCI |
| 语种 | 英语 |
| 公开日期 | 2015-11-02 |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/28138]  |
| 专题 | 化学研究所_分子识别与功能实验室 |
| 作者单位 | 1.Chinese Acad Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing Natl Lab Mol Sci BNLMS, Beijing 100190, Peoples R China 2.Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan 3.Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England 4.Shandong Univ, State Key Lab Microbial Technol, Jinan 250100, Peoples R China 5.Shandong Univ, Natl Glycoengn Res Ctr, Jinan 250100, Peoples R China 6.Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Yi-Xian,Shimada, Yousuke,Adachi, Isao,et al. Fluorinated and Conformationally Fixed Derivatives of L-HomoDMDP: Synthesis and Glycosidase Inhibition[J]. JOURNAL OF ORGANIC CHEMISTRY,2015,80(10):5151-5158. |
| APA | Li, Yi-Xian.,Shimada, Yousuke.,Adachi, Isao.,Kato, Atsushi.,Jia, Yue-Mei.,...&Yu, Chu-Yi.(2015).Fluorinated and Conformationally Fixed Derivatives of L-HomoDMDP: Synthesis and Glycosidase Inhibition.JOURNAL OF ORGANIC CHEMISTRY,80(10),5151-5158. |
| MLA | Li, Yi-Xian,et al."Fluorinated and Conformationally Fixed Derivatives of L-HomoDMDP: Synthesis and Glycosidase Inhibition".JOURNAL OF ORGANIC CHEMISTRY 80.10(2015):5151-5158. |
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来源：化学研究所
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