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Assignment of absolute configuration of sulfinyl dilactones: Optical rotations and H-1 NMR experiment and DFT calculations
Fu, Gang1; Doerksen, Robert J.1,2; Xu, Ping3
关键词Sulfinyl Dilactones Optical Rotation Density Functional Theory H-1 Nmr Diastereomer Absolute Configuration
刊名JOURNAL OF MOLECULAR STRUCTURE
2011-02-22
DOI10.1016/j.molstruc.2010.11.076
987期:1-3页:166-173
收录类别SCI
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Physical
研究领域[WOS]Chemistry
关键词[WOS]AB-INITIO CALCULATION ; DENSITY-FUNCTIONAL METHODS ; PROTON CHEMICAL-SHIFTS ; CHIROPTICAL PROPERTIES ; PROTEASOME INHIBITORS ; PYRAMIDAL INVERSION ; ORGANIC-MOLECULES ; SULFUR ; STATE ; NMR
英文摘要

In previous work, two sulfinyl dilactone compounds were synthesized as key intermediates in the development of new proteasome inhibitors. Two stereogenic centers were introduced during synthesis, including one chiral sulfoxide in a five-membered ring. The absolute configurations (AC) of these two compounds were hard to determine just based on experimental techniques. Therefore, theoretical calculations of chiro-optical and spectroscopic features were used to determine stereochemistry. Ab initio calculations at DFT/B3LYP/6-31G (d, p) level of theory obtained satisfactory agreement with the experimental results. Furthermore, there was good agreement between the calculations of optical rotations and hydrogen chemical shifts in H-1 NMR spectra for the final AC assignment as (1′S, 2R, 5R)- and (1′S, 2S, 5S)-5-[1′-(t-Boc-amino)-3′-methylbutyl]-1,3,2-dioxathiolane-2-oxide. This is a successful application of ab initio calculations for the AC assignment for small flexible molecules. (C) 2010 Elsevier B.V. All rights reserved.

语种英语
WOS记录号WOS:000287832000022
项目编号C06 RR-14503-01 ; 30772650 ; 20772008
资助机构University of Mississippi ; NIH National Center for Research Resources ; National Natural Science Foundation of China
引用统计
被引频次:6[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/49973
专题北京大学药学院_药物化学系
作者单位1.Univ Mississippi, Sch Pharm, Dept Med Chem, University, MS 38677 USA
2.Univ Mississippi, Pharmaceut Sci Res Inst, University, MS 38677 USA
3.Peking Univ, Hlth Sci Ctr, Sch Pharmaceut Sci, Dept Med Chem, Beijing 100191, Peoples R China
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GB/T 7714
Fu, Gang,Doerksen, Robert J.,Xu, Ping. Assignment of absolute configuration of sulfinyl dilactones: Optical rotations and H-1 NMR experiment and DFT calculations[J]. JOURNAL OF MOLECULAR STRUCTURE,2011,987(1-3):166-173.
APA Fu, Gang,Doerksen, Robert J.,&Xu, Ping.(2011).Assignment of absolute configuration of sulfinyl dilactones: Optical rotations and H-1 NMR experiment and DFT calculations.JOURNAL OF MOLECULAR STRUCTURE,987(1-3),166-173.
MLA Fu, Gang,et al."Assignment of absolute configuration of sulfinyl dilactones: Optical rotations and H-1 NMR experiment and DFT calculations".JOURNAL OF MOLECULAR STRUCTURE 987.1-3(2011):166-173.
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