Configurations and conformations of sanguinarine and chelerythrine free bases stereoisomers

被引：19

作者：

Tousek, J

Dommisse, R

Dostál, J

Zák, Z

Pieters, L

Marek, R

机构：

[1] Masaryk Univ, Fac Sci, Dept Theoret & Phys Chem, CZ-61137 Brno, Czech Republic

[2] Univ Antwerp, RUCA, Dept Chem, B-2020 Antwerp, Belgium

[3] Masaryk Univ, Fac Med, Dept Biochem, CZ-66243 Brno, Czech Republic

[4] Masaryk Univ, Dept Inorgan Chem, CZ-61137 Brno, Czech Republic

[5] Univ Instelling Antwerp, Dept Pharmaceut Sci, B-2610 Antwerp, Belgium

[6] Masaryk Univ, Fac Sci, Natl Ctr Biomol Res, CZ-61137 Brno, Czech Republic

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2002年 / 613卷 / 1-3期

关键词：

sanguinarine; chelerythrine; NMR spectroscopy; X-ray crystallography; quantum chemical calculations;

D O I：

10.1016/S0022-2860(02)00138-2

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 configurations and conformations of bimolecular aminoacetals of benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine were investigated by NMR spectroscopy, quantum chemical calculations, and X-ray analysis. The results of the complete computational conformational analysis, the calculation of the chemical shielding of the considerably populated conformers, the determination of averaged chemical shifts and comparison with experimental NMR chemical shifts observed in solution are reported. Based on these results, the relative configurations at the stereogenic centers of two diastereomers of bis(dihydrosanguinarinyl) ether were determined. The structure of the major diastereomer of bis(dihydrosanguinarinyl) ether was confirmed by X-ray analysis and specified for the solid state. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：103 / 113

页数：11

共 31 条

[1] NATURAL ABUNDANCE N-15 NMR BY ENHANCED HETERONUCLEAR SPECTROSCOPY [J].