title: Synthesis and evaluation of two coumarin-type derivatization reagents for fluorescence detection of chiral amines and chiral carboxylic acids.
abstract: The synthesis of two fluorescent coumarin-type chiral derivatization agents (4 and 11) is reported. A chiral side chain was introduced at position 7 of the coumarin via Mitsunobu reaction. The two coumarins bear in this side chain either a free amino group or a carboxyl group, making them useful for further transformations. Conjugates of chiral prototype drugs with 4 or 11 were prepared by amide coupling of the analyte's carboxyl group to the reagent's amine group, or vice versa. The separation of seven diastereomeric conjugates through achiral high-performance liquid chromatography (HPLC) on a common C18 column is demonstrated.
authors.affiliation: Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, Bonn, Germany.
authors.forename: Matthias D
authors.initials: MD
authors.lastname: Mertens
authors.forename: Michael
authors.initials: M
authors.lastname: Gütschow
mesh_terms: D000588:Amines / Q000032:analysis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000032:analysis* / Q000737:chemistry; D002623:Chemistry Techniques, Analytical; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D002264:Carboxylic Acids; D003374:Coumarins; D005456:Fluorescent Dyes; D011422:Propionates; C030123:coumarin; C029658:propionic acid
keywords: Mitsunobu reaction; chiral coumarins; diastereomer separation; fluorescence detection; precolumn derivatization; reversed-phase high-performance liquid chromatography