Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction.

Chem Commun (Camb)

Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.

Published: August 2019

Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a powerful control element for conformationally homogenous peptide macrocycles.

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Source
http://dx.doi.org/10.1039/c9cc05934bDOI Listing

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