Synthesis and Chemical Proteomic Studies of Photoactive Pyoverdin D Probes

Raju Adepu adepu@post.bgu.ac.il Rambabu Dandela Roi Mashiach Aviad Mandabi Alex Yashkin Michael M. Meijler
Department of Chemistry and The National Institute for Biotechnology in the Negev, Ben-Gurion University of the Negev, Be’er Sheva, Israel

Pyoverdin is the primary high-affinity Fe binding siderophore produced by fluorescent Pseudomonas species.1 Here we developed the synthesis of two pyoverdin chemical probes i.e., pyoverdin diazirine and pyoverdin mimic benzophenone probe (Figure 1). These probes contain a photoreactive group (diazirine/benzophenone), and a `click` handle which has allowed us to perform chemical proteomics experiments in order toidentify putative unknown proteins that bind pyoverdin.2 We identified several proteins that thus far had not been annotated as pyoverdin binders.

Figure 1. Chemical structures of probes 1 and 2

Figure 1. Chemical structures of probes 1 and 2

REFERENCES

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  2. (a) R. Mashiach and M. M. Meijler, Org Lett, 2013, 15, 1702-1705 (b) N. Amara, R. Mashiach, D. Amar, P. Krief, S. A. Spieser, M. J. Bottomley, A. Aharoni and M. M. Meijler, J Am Chem Soc, 2009, 131, 10610-10619 (c) J. Rayo, N. Amara, P. Krief and M. M. Meijler, J Am Chem Soc, 2011, 133, 7469-7475 (d) L. Dubinsky, A. Delago, N. Amara, P. Krief, J. Rayo, T. Zor, V. V. Kravchenko and M. M. Meijler, Chem Commun, 2013, 49, 5826-5828 (e) R. Dandela, R. Mashiach, R. Adepu, R. Gregor, M. Athamna, E. Zecharia, O. Ernst, T. Zor and M. M. Meijler, Chem Commun, 2017, 53, 3842-3845.








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