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Design and Synthesis of New Protease‐Triggered CO‐Releasing Peptide–Metal‐Complex Conjugates
Author(s) -
Sitnikov Nikolay S.,
Malysheva Yulia B.,
Fedorov Alexey Yu.,
Schmalz HansGünther
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901206
Subject(s) - chemistry , linker , combinatorial chemistry , peptide , conjugate , peptide synthesis , solid phase synthesis , protease , lysine , cleavage (geology) , molecule , stereochemistry , organic chemistry , amino acid , biochemistry , enzyme , engineering , operating system , mathematical analysis , mathematics , geotechnical engineering , fracture (geology) , computer science
Aiming at the development of novel protease‐triggered CO‐releasing molecules (PT‐CORMs) we designed a series of oxycyclohexadiene‐Fe(CO) 3 complexes, which are connected through a self‐immolative linker with a plasmin‐specifying peptide unit. The challenging synthesis of these compounds was elaborated employing a combination of solid‐phase peptide synthesis and solution chemical synthesis. Late‐stage attachment of the organometallic unit and Pd‐catalyzed cleavage of an alloc‐protected lysine side chain afforded the target compounds in good yields and high purity.