Phenylalanyl-aminocyclophosphamides as model prodrugs for proteolytic activation: synthesis, stability, and stereochemical requirements for enzymatic cleavage.

@article{Jiang2007PhenylalanylaminocyclophosphamidesAM,
  title={Phenylalanyl-aminocyclophosphamides as model prodrugs for proteolytic activation: synthesis, stability, and stereochemical requirements for enzymatic cleavage.},
  author={Yongying Jiang and Longqin Hu},
  journal={Bioorganic & medicinal chemistry letters},
  year={2007},
  volume={17 2},
  pages={517-21}
}
4-Aminocyclophosphamide (4-NH2-CPA, 7) was proposed as a prodrug moiety of phosphoramide mustard. Four diastereomers of phenylalanine-conjugates of 4-NH2-CPA were synthesized and their stereochemistry was assigned based on chromatographic and spectroscopic data. All diastereomers were stable in phosphate buffer but only the cis-(4R)-isomer of 15 was… CONTINUE READING