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- Title
Enantioseparation on Riboflavin Derivatives Chemically Bonded to Silica Gel as Chiral Stationary Phases for HPLC.
- Authors
Kumano, Daisuke; Iwahana, Soichiro; Iida, Hiroki; Shen, Chengshuo; Crassous, Jeanne; Yashima, Eiji
- 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 (HPLC). The 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 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.
- Subjects
SEPARATION of enantiomers; VITAMIN B2; SILICA gel; CHIRAL stationary phases; CHIRAL recognition; HIGH performance liquid chromatography
- Publication
Chirality, 2015, Vol 27, Issue 8, p507
- ISSN
0899-0042
- Publication type
Article
- DOI
10.1002/chir.22452