Issue 71, 2019
From the journal:

Chemical Communications

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

Akitake Yamaguchi,a   Sherif J. Kaldas, ORCID logo a   Solomon D. Appavoo,a   Diego B. Diaz ORCID logo a  and  Andrei K. Yudin ORCID logo *a  

* Corresponding authors

a Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada
E-mail: andrei.yudin@utoronto.ca

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/C9CC05934B
Article type
Communication
Submitted
30 Jul 2019
Accepted
02 Aug 2019
First published
02 Aug 2019

Chem. Commun., 2019,55, 10567-10570

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

A. Yamaguchi, S. J. Kaldas, S. D. Appavoo, D. B. Diaz and A. K. Yudin, Chem. Commun., 2019, 55, 10567 DOI: 10.1039/C9CC05934B

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