NDLI: LC Separation of Enantiomers on Silica-Bonded Thiostrepton Derivatives

Content Provider	Springer Nature Link
Author	Hsiao, Ya Li Chen, Shushi
Copyright Year	2009
Abstract	The macrocyclic antibiotic thiostrepton has been structurally modified with achiral reagents containing aromatic groups and isocyanate or isothiocyanate-terminated linkages to improve its selectivity in the LC resolution of aromatic enantiomers in polar–organic mode. The enantiomer resolutions achieved could not be reproduced either with underivatized thiostrepton or with the rifamycin SV stationary phase prepared by use of the same reaction procedures. Maximum enantioselectivity was achieved by optimizing the number of achiral derivatizing groups attached to thiostrepton. Chromatographic data for resolution of enantiomers containing aromatic groups suggest that the enhanced resolution is highly dependent on the π–π interaction between the analyte and the chiral selector. A mechanistic study entailing resolution of amino acid derivatives also indicated that analyte structure affects the strength of the π–π interaction and is crucial for chiral recognition to be possible. Other effects, for example steric hindrance, dipole–dipole interaction, and hydrogen bonding with the isocyanate and isothiocyanate functional groups of reagents also facilitate resolution.
Starting Page	1031
Ending Page	1038
Page Count	8
File Format	PDF
ISSN	00095893
Journal	Chromatographia
Volume Number	70
Issue Number	7-8
e-ISSN	16121112
Language	English
Publisher	Vieweg Verlag
Publisher Date	2009-09-11
Publisher Place	Wiesbaden
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Column liquid chromatography Enantiomer separation Chemical derivatization Aromatic carboxylic acids Alkylisothiocyanate-derivatized amino acids Thiostrepton Isocyanate and isothiocyanate Measurement Science and Instrumentation Plant Sciences Biochemistry Pharmacy Organic Chemistry Analytical Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Analytical Chemistry Biochemistry Clinical Biochemistry

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