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With the discovery of an increasing number of biologically active peptides and peptide mimetics (
1
–
3
), there is a pressing need for the development of strategies to deliver these biologically active compounds to the desired site of action. The preceding two chapters have described two methods of making esterase-sensitive cyclic prodrugs of peptides. In this chapter, we wish to describe a third method of making esterase-sensitive cyclic prodrugs of peptides using DADLE, an opioid peptide (
4
–
7
), as an example.