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β-cyclodextrin derivatives bearing benzoyl (β-CD-1) and naphthoyl (β-CD-2) moieties have been synthesized from salicylic acid and 3-hydroxy-2-naphthoic acid by a convenient method in 60% and 58% yields, respectively, and were tested for enantiomeric recognition of amino acid ester derivatives. Their ability to discriminate between various L-/Damino acid methyl ester hydrochloride salts was examined using the H NMR titration method in DMSO-d6 at 25 C. βCD-2 produced a fairly good discrimination of tryptophan ester salts with a binding constant of 4041 M for L-salt compared with 2864 M for D-salt, which corresponds to a difference of 0.21 kcal mol in binding free energies. The binding free energies obtained from molecular dynamic calculation by MM/PB(GB)SA are consistent with those obtained from the experimental results.

Enantiomeric recognition of amino acid ester salts by β-cyclodextrin derivatives: an experimental and computational study