Enantioseparation on Riboflavin Derivatives Chemically Bonded to Silica Gel as Chiral Stationary Phases for HPLC. Issue 8 (28th April 2015)

• Record Type: Journal Article
• Authors: Kumano, Daisuke; Iwahana, Soichiro; Iida, Hiroki; Shen, Chengshuo; Crassous, Jeanne; Yashima, Eiji
• Is Part Of: Chirality. Volume 27:Issue 8(2015)
• Page Start: 507
• Page End: 517
• Publication Date: 2015-04-28
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22452
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>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 <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">liquid chromatography</named-content> (HPLC). The <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chiral recognition</named-content> 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 <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chiral recognition</named-content> 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. <italic>Chirality 27:507–517</italic>, <italic>2015</italic>. © 2015 Wiley Periodicals, Inc.</p> </abstract>