Chiral separation of 9-fluorenylmethyl chloroformate- and dansyl chloride-derivatized D,L-serine by gamma-cyclodextrin-bonded high-performance liquidchromatography

When acetate buffer was used in chiral separation Of D,L-serine derivatives using a gamma -cyclodextrin (CD) column, both retention factor and resolut ion were high below the pK(a) of acetic acid and decreased sharply as the p H approached the pK(a). A similar result was obtained by increasing the buf fer concentration at a fixed pH. These observations suggest that hydrogen b onding interaction between the carboxylate group of the amino acid and the secondary hydroxyl groups at the CD rim plays an important role in chiral s eparation and is disrupted by the buffer anion. (C) 2001 Elsevier Science B .V. All rights reserved.