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学科主题: 药学
题名:
Assignment of absolute configuration of sulfinyl dilactones: Optical rotations and H-1 NMR experiment and DFT calculations
作者: 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
发表日期: 2011-02-22
DOI: 10.1016/j.molstruc.2010.11.076
卷: 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
所属项目编号: C06 RR-14503-01 ; 30772650 ; 20772008
项目资助者: University of Mississippi ; NIH National Center for Research Resources ; National Natural Science Foundation of China
WOS记录号: WOS:000287832000022
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/49973
Appears in Collections:北京大学药学院_药物化学系_期刊论文

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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

Recommended Citation:
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.
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