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Chiral stationary phases for separation of intermedine and lycopsamine enantiomers from Symphytum uplandicum
Author(s) -
Pawar Rahul S.,
Grundel Erich,
Mazzola Eugene,
White Kevin D.,
Krynitsky Alexander J.,
Rader Jeanne I.
Publication year - 2010
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200900611
Subject(s) - chromatography , diethylamine , enantiomer , pyrrolizidine , chemistry , pyrrolizidine alkaloid , high performance liquid chromatography , chiral column chromatography , methanol , alkaloid , organic chemistry , stereochemistry
Enantioseparation of the pyrrolizidine alkaloid isomers intermedine and lycopsamine, isolated from Symphytum uplandicum , is discussed. The separatory power of two immobilized carbohydrate‐based chiral HPLC columns, Chiralpak IA and IC, in different chromatographic conditions is compared. The study demonstrated the importance of solvent and column selection while developing such chiral HPLC separation methods. The baseline HPLC separation of the two alkaloid isomers in preparatory scale is reported for the first time. The optimized separations were achieved on a Chiralpak IA column with mobile phases of ACN/methanol (80:20) and methanol/methyl‐ t ‐butyl ether (90:10), both containing 0.1% diethylamine.