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Issue 10, 2015
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Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway

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Abstract

Aziridine aldehyde dimers, peptides, and isocyanides participate in a multicomponent reaction to yield peptide macrocycles. We have investigated the selectivity and kinetics of this process and performed a detailed analysis of its chemoselectivity. While the reactants encompass all of the elements of the traditional Ugi four-component condensation, there is a significant deviation from the previously proposed mechanism. Our results provide evidence for an imidoanhydride pathway in peptide macrocyclization and lend justification for the diastereoselectivity and high effective molarity observed in the reaction.

Graphical abstract: Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway

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Supplementary files

Article information


Submitted
01 Jun 2015
Accepted
07 Jul 2015
First published
07 Jul 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 5446-5455
Article type
Edge Article
Author version available

Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway

S. Zaretsky, J. L. Hickey, J. Tan, D. Pichugin, M. A. St. Denis, S. Ler, B. K. W. Chung, C. C. G. Scully and A. K. Yudin, Chem. Sci., 2015, 6, 5446
DOI: 10.1039/C5SC01958C

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