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Development of a Reduction‐Responsive Amino Acid that Induces Peptide Bond Cleavage in Hypoxic Cells
Author(s) -
Shigenaga Akira,
Ogura Keiji,
Hirakawa Hiroko,
Yamamoto Jun,
Ebisuno Koji,
Miyamoto Licht,
Ishizawa Keisuke,
Tsuchiya Koichiro,
Otaka Akira
Publication year - 2012
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201200141
Subject(s) - prodrug , peptide , cleavage (geology) , peptide bond , chemistry , amino acid , nitro , bond cleavage , stereochemistry , hypoxia (environmental) , combinatorial chemistry , biochemistry , catalysis , biology , organic chemistry , oxygen , paleontology , alkyl , fracture (geology)
Hypoxia‐responsive amino acids are indispensable in the preparation of hypoxic tumor‐specific peptidyl prodrugs. In this paper, the 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.