Copper-Mediated Radiocyanation of Unprotected Amino Acids and Peptides.

ABSTRACT: This report describes a copper-mediated radiocyanation of aryl halides that is applicable to complex molecules. This transformation tolerates an exceptionally wide range of functional groups, including unprotected amino acids. As such, it enables the site-specific introduction of [¹¹C]CN into peptides at an iodophenylalanine residue. The use of a diamine-ligated copper(I) mediator is crucial for achieving high radiochemical yield under relatively mild conditions, thus limiting racemization and competing side reactions of other amino acid side chains. The reaction has been scaled and automated to deliver radiolabeled peptides, including analogues of adrenocorticotropic hormone 1-27 (ACTH) and nociceptin (NOP). For instance, this Cu-mediated radiocyanation was leveraged to prepare

SUBMITTER: Sharninghausen LS 

PROVIDER: S-EPMC9887455 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature