Absolute configuration and conformational analysis of sesquiterpene lactone glycoside studied by vibrational circular dichroism spectroscopy

被引：6

作者：

Michalski, Oskar ^{[1
]}

Kisiel, Wanda ^{[2
]}

Michalska, Klaudia ^{[2
]}

Setnicka, Vladimir ^{[3
]}

Urbanova, Marie ^{[4
]}

机构：

[1] Univ Agr, Dept Chem, PL-31149 Krakow, Poland

[2] Polish Acad Sci, Inst Pharmacol, Dept Phytochem, PL-31343 Krakow, Poland

[3] Inst Chem Technol, Dept Analyt Chem, CR-16628 Prague 6, Czech Republic

[4] Inst Chem Technol, Dept Phys & Measurement, CR-16628 Prague 6, Czech Republic

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2007年 / 871卷 / 1-3期

关键词：

VCD spectroscopy; Crepis species; sesquiterpene lactones; absolute configuration; conformational analysis;

D O I：

10.1016/j.molstruc.2007.01.047

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The absolute configuration of the guaiane-type sesquiterpene lactone 8-epiisolippidiol-3-O-beta-D-glucopyranoside, isolated from plants of the genus Crepis, and the predominant solution-state conformation in CD3OD were determined by comparison of experimental and calculated VCD spectra. It has been found that the reported stereostructure of the compound corresponds to its absolute configuration. (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：67 / 72

页数：6

共 20 条

[1] ADEKENOV SM, 1992, CHEM NAT COMPD, V5, P562
[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[3] (3R,4S)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine:: Conformation and structure monitoring by vibrational circular dichroism
Bour, P
Navrátilová, H
Setnicka, V
Urbanová, M
Volka, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 161 - 168
[4] STRUCTURE OF SESQUITERPENIC LACTONES OF SOME SPECIES OF SUBTRIBE CENTAUREINAE DUMORT
BUDESINSKY, M
NOWAK, G
RYCHLEWSKA, U
HODGSON, DJ
SAMAN, D
DANIEWSKI, WM
DROZDZ, B
HOLUB, M
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1994, 59 (05) : 1175 - 1202
[5] Synthesis and chiroptical properties of enantiopure tricyclo[4.3.0.03,8]nonane-4,5-dione (twistbrendanedione)
Butkus, E
Zilinskas, A
Stoncius, S
Rozenbergas, R
Urbanová, M
Setnicka, V
Bour, P
Volka, K
[J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (06) : 633 - 638
[6] Determination of absolute configuration using vibrational circular dichroism spectroscopy: phenyl glycidic acid derivatives obtained via asymmetric epoxidation using oxone and a keto bile acid
Devlin, FJ
Stephens, PJ
Bortolini, O
[J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (15) : 2653 - 2663
[7] Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism
Freedman, TB
Cao, XL
Dukor, RK
Nafie, LA
[J]. CHIRALITY, 2003, 15 (09) : 743 - 758
[8] Frisch M.J., 1998, GAUSSIAN 98
[9] Kisiel W, 2001, Z NATURFORSCH C, V56, P961
[10] Kisiel W, 2002, POL J CHEM, V76, P1571

← 1 2 →