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Enantioseparation by HPLC using phenylcarbonate, benzoylformate, p ‐toluenesulfonylcarbamate, and benzoylcarbamates of cellulose and amylose as chiral stationary phases
Author(s) -
Ikai Tomoyuki,
Yamamoto Chiyo,
Kamigaito Masami,
Okamoto Yoshio
Publication year - 2005
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20168
Subject(s) - chemistry , cellulose , high performance liquid chromatography , chirality (physics) , hydrogen bond , amylose , organic chemistry , chromatography , chiral column chromatography , chiral stationary phase , stereochemistry , molecule , chiral symmetry , nambu–jona lasinio model , quark , physics , quantum mechanics , starch
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.