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Enantioseparation by HPLC using phenylcarbonate, benzoylformate, p-toluenesulfonylcarbamate, and benzoylcarbamates of cellulose and amylose as chiral stationary phases

✍ Scribed by Tomoyuki Ikai; Chiyo Yamamoto; Masami Kamigaito; Yoshio Okamoto

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
385 KB
Volume
17
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

Phenylcarbonate, benzoylformate, and p‐toluenesulfonylcarbamate of cellulose and five new benzoylcarbamate derivatives of both cellulose and amylose were synthesized and their chiral recognition abilities were evaluated as chiral stationary phases (CSPs) for high‐performance liquid chromatography (HPLC). Cellulose benzoylcarbamate has a higher chiral recognition ability compared to phenylcarbonate, p‐toluenesulfonylcarbamate, and benzoylformate of cellulose. The benzoylcarbamate derivatives exhibited a characteristic chiral recognition for the racemates, which bear a hydrogen atom capable of hydrogen bonding to the carbonyl group of the benzoylcarbamates. The structures of the benzoylcarbamates were investigated by CD spectroscopy. Chirality 17:299–304, 2005. © 2005 Wiley‐Liss, Inc.

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