Sonogashira and "Click" reactions for the N-terminal and side-chain functionalization of peptides with [Mn(CO)3(tpm)]+-based CO releasing molecules (tpm = tris(pyrazolyl)methane).
A recently identified photoactivatable CO releasing molecule (CORM) based on [Mn(CO)(3)(tpm)](+) was conjugated to functionalized amino acids and model peptides using the Pd-catalyzed Sonogashira cross-coupling and the alkyne-azide 1,3-dipolar cycloaddition ("Click reaction"). Both were found to be fully compatible with all functional groups present. The CORM-peptide conjugates were isolated in reasonable yield and high purity, as indicated by IR spectroscopy, ESI mass spectrometry and RP-HPLC. The myoglobin assay was used to demonstrate that they have CO release properties identical those of the parent compound. This work thus opens the way for a targeted delivery of CORMs to cellular systems.
Pfeiffer
Hendrik
H
Lehrstuhl für Anorganische Chemie I-Bioanorganische Chemie, Ruhr-Universität Bochum NC 3/74, Bochum, Germany.
Rojas
Alfonso
A
Niesel
Johanna
J
Schatzschneider
Ulrich
U
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D002248:Carbon Monoxide / Q000378:metabolism*; D002254:Carbonates / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D006736:Horses; D008345:Manganese / Q000737:chemistry* / Q000378:metabolism*; D009211:Myoglobin / Q000378:metabolism; D010165:Palladium / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D000480:Alkynes; D000596:Amino Acids; D001386:Azides; D002254:Carbonates; D009211:Myoglobin; D010455:Peptides; D011720:Pyrazoles; C515920:tris(pyrazolyl)methane; D008345:Manganese; D010165:Palladium; D002248:Carbon Monoxide; C045327:manganese carbonate