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Direct Chiral Separation of Tryptophan Analogues Using Heptakis(3-O-Methyl)-β-Cyclodextrin-Bonded Stationary Phase in Reversed-Phase Liquid Chromatography

✍ Scribed by Jae Wook Ryu; Hae Sung Chang; Young Kwan Ko; Jae Chun Woo; Dong Wan Koo; Dae Whang Kim

Publisher: Elsevier Science
Year: 1999
Tongue: English
Weight: 30 KB
Volume: 63
Category: Article
ISSN: 0026-265X
DOI: 10.1006/mchj.1999.1779

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✦ Synopsis

For the direct separation of racemic tryptophan analogues by reversed-phase liquid chromatography, native ␤-cyclodextrin (CD), heptakis(3-O-methyl)-␤-CD, and heptakis(2,3-di-O-methyl)-␤-CD chiral stationary phases were examined. Direct separation of various tryptophan analogues was accomplished with heptakis(3-O-methyl)-␤-CD stationary phase. It was observed that the position of substituents affects retention and enantioselectivity of tryptophan analogues. Substitution at the 6-position (e.g., 6-methyl-DL-tryptophan and 6-fluoro-DL-tryptophan) significantly increased retention and enantioselectivity.

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## Abstract The characteristics of the new chiral stationary phase heptakis(2,3‐di‐__O__‐methyl‐6‐__O__‐__tert__‐butyldimethylsilyl)‐β‐cyclodextrin are outlined and compared with permethyl‐ and perethyl‐β‐cyclodextrins.