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

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...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2019-08, Vol.55 (71), p.1567-157
Hauptverfasser:	Yamaguchi, Akitake, Kaldas, Sherif J, Appavoo, Solomon D, Diaz, Diego B, Yudin, Andrei K
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Amides - chemistry Amines - chemistry Aziridines - chemistry Boronic Acids - chemistry Crystallography Cyclization Hydrogen bonds Macrocyclic Compounds - chemical synthesis Peptides Peptides, Cyclic - chemical synthesis
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Beschreibung
Zusammenfassung:	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. Synthesis and the structural analysis of conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction are reported.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c9cc05934b