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There is now a CONTENT FREEZE for Mercury while we switch to a new platform. It began on Friday, March 10 at 6pm and will end on Wednesday, March 15 at noon. No new content can be created during this time, but all material in the system as of the beginning of the freeze will be migrated to the new platform, including users and groups. Functionally the new site is identical to the old one. webteam@gatech.edu
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Title:
Chemical strategies for breaking and making carbon–nitrogen bonds
Abstract:
I. C-N bond breaking: Amines are ubiquitous functional groups that are simple to prepare and functionalize. We show that tertiary amines can template reductive cyclization reactions, forming biaryl and bibenzyl carbon–carbon bonds. These cyclic amine products can undergo carbon–carbon bond-forming amine rearrangement and deaminative contraction reactions, providing efficient access to polycyclic (hetero)aromatic natural products. These strategies and our understanding of deaminative mechanisms will be presented.
II. C-N bond making: Residue-selective methods for peptide modification and cyclization are useful for the development of therapeutic peptides with improved metabolic stability properties. The Roberts laboratory draws inspiration from cyclic peptide natural products that exhibit a host of promising biological properties. Motivated by the phenolic linkages found in both the arylomycin and vancomycin families of natural products, we have developed methods that leverage the in situ generation of 1,2,4-triazoline-3,5-dione moieties on native peptides to achieve tyrosine-selective cyclizations. Detailed accounts of these methods and their applications will be presented.
