The ability of α-N-acetylcycloserine to participate in acyl transfer reactions has been investigated. The reaction with cinnamoylimidazole yields a stable monocinnamoyl intermediate, while that with p-nitrophenyl acetate yields a derivative which undergoes facile deacylation. The kinetics of acylation of α-N-acetylcycloserine and of the deacylation of its acetyl intermediate are reported.