Development of a Reduction‐Responsive Amino Acid that Induces Peptide Bond Cleavage in Hypoxic Cells

Utilization of a hypoxia-responsive amino acid is indispensable in the preparation of hypoxic tumor-specific peptidyl prodrugs. Bioreduction of a nitro group is among the most attractive triggering reactions in the hypoxia-responsive prodrugs. In this paper, design and synthesis of a reduction-responsive amino acid that induces peptide bond cleavage after reduction of the nitro group are described. Application to hypoxia-responsive peptide bond cleavage system is also reported.

This is the peer reviewed version of the following article: Shigenaga, A. , Ogura, K. , Hirakawa, H. , Yamamoto, J. , Ebisuno, K. , Miyamoto, L. , Ishizawa, K. , Tsuchiya, K. and Otaka, A. (2012), Development of a Reduction‐Responsive Amino Acid that Induces Peptide Bond Cleavage in Hypoxic Cells. ChemBioChem, 13: 968-971. doi:10.1002/cbic.201200141, which has been published in final form at https://doi.org/10.1002/cbic.201200141. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.