Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides
- 12 July 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (16), 6189-6193
- https://doi.org/10.1021/acs.orglett.1c01622
Abstract
Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C–N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.Keywords
Funding Information
- Division of Chemistry (CHE-1752654)
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