Phosphinic Peptides as Potent Inhibitors of Zinc-Metalloproteases

  • Dimitris GeorgiadisEmail author
  • Vincent Dive
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 360)


The development of transition-state analogs is a major objective in enzymology, not only for developing potent inhibitors of enzymes but also for dissecting enzyme catalytic mechanisms. Phosphinic peptides, which share closed structural similarities with the transition-state of peptide substrate upon hydrolysis, have thus been considered for identifying potent inhibitors of proteases. Focusing on the zinc-proteases family, this review presents the most important synthetic efforts performed to obtain the desired compounds. Crystal structures of the phosphinic peptides in interaction with their zinc-protease targets are reported to illustrate the structural features which may explain the potency of these compounds and how they contribute to uncover key enzyme catalytic residues. Based on a remarkable metabolic stability, phosphinic peptides can be used to probe the in vivo function of zinc-proteases. Progress on chemistry and better understanding on the functional roles of zinc-proteases should allow transferring these compounds from shelf to clinic.


Inhibitors Phosphinic peptides Zn-proteases 


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Copyright information

© Springer International Publishing Switzerland 2014

Authors and Affiliations

  1. 1.Department of Chemistry, Laboratory of Organic ChemistryUniversity of AthensAthensGreece
  2. 2.CEA-Saclay, Service d’Ingénierie Moléculaire des Protéines Labex LERMIT, CEA-DSV-iBiTecSGif/YvetteFrance

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