Trifluoromethyldiazirinylphenyldiazenes: New hemoprotein active-site probes

RA Tschirret-Guth, KF Medzihradszky…

Index: Tschirret-Guth, Richard A.; Medzihradszky, Katalin F.; Ortiz De Montellano, Paul R. Journal of the American Chemical Society, 1999 , vol. 121, # 20 p. 4731 - 4737

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Citation Number: 5

Abstract

The photoactivatable trifluoromethyldiazirinylphenyldiazene probes 1a and 2a have been synthesized, and their utility in the mapping of hemoprotein active sites has been validated with myoglobin (Mb). Reaction of the probes with Mb yields Fe-aryl adducts. Photolysis of these adducts unmasks a carbene that cross-links to active-site protein residues. Migration of the aryl group from the iron to a porphyrin nitrogen then attaches the porphyrin ...