Carboxylic acids were found to be easily coupled onto NH2-β-CD under the same conditions as the amino acids. Compounds 13-16 were successfully synthesized in ≥68 % yields. This allows for cyclodextrin to be modified with an even larger variety of functionalities, which are useful both as precursors for further synthesis and to achieve enhanced diversity of the binding data for use in force field optimization. The propargyl (Compound 13) and azide (Compound 14) groups are accessible precursors to further expand the diversity of cyclodextrin analogues through click chemistry reactions on the secondary face of β-CD.