Design and Synthesis of New Protease‐Triggered CO‐Releasing Peptide–Metal‐Complex Conjugates. Issue 40 (17th October 2019)

• Record Type: Journal Article
• Authors: Sitnikov, Nikolay S.; Malysheva, Yulia B.; Fedorov, Alexey Yu.; Schmalz, Hans‐Günther
• Is Part Of: European journal of organic chemistry. Issue 40(2019)
• Page Start: 6830
• Page End: 6837
• Publication Date: 2019-10-17
• Subjects: CO releasing molecules -- Peptides -- Iron complexes -- Enzymes -- Protecting groups; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901206
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : Potentially tissue‐selective protease‐activated CO‐releasing molecules (PT‐CORMs) were designed and synthesized by conjugating a protease‐specifying peptide to an oxy‐cyclohexadiene‐Fe(CO)3 unit through a self‐immolative linker.