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Enantioseparation on Riboflavin Derivatives Chemically Bonded to Silica Gel as Chiral Stationary Phases for HPLC
Author(s) -
Kumano Daisuke,
Iwahana Soichiro,
Iida Hiroki,
Shen Chengshuo,
Crassous Jeanne,
Yashima Eiji
Publication year - 2015
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.22452
Subject(s) - chemistry , helicene , enantiomer , silica gel , riboflavin , high performance liquid chromatography , chiral stationary phase , chirality (physics) , organic chemistry , chromatography , molecule , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Abstract Acetylated and/or 3,5‐dimethylphenylcarbamated riboflavins were prepared and the resulting riboflavin derivatives as well as natural riboflavin were regioselectively immobilized on silica gel through chemical bonding at the 5’‐O‐ or 3‐N‐position of the riboflavin to develop novel chiral stationary phases (CSPs) for enantioseparation by high‐performance liquid chromatography (HPLC). The chiral recognition abilities of the obtained CSPs were significantly dependent on the structures of the riboflavin derivatives, the position of the chemical bonding on the silica gel, and the structures of the racemic compounds. The CSPs bonded at the 5’‐O‐position on the silica gel tended to well separate helicene derivatives, while the CSPs bonded at the 3‐N‐position composed of acetylated and 3,5‐dimethylphenylcarbamated riboflavins showed a better resolving ability toward helicene derivatives and bulky aromatic racemic alcohols, respectively, and some of them were completely separated into the enantiomers. The observed difference in the chiral recognition abilities of these riboflavin‐based CSPs is discussed based on the difference in their structures, including the substituents of riboflavin and the positions immobilized on the silica gel. Chirality 27:507–517 , 2015 . © 2015 Wiley Periodicals, Inc.