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Chemistry. 2015 Jun 15;21(25):9249-55. doi: 10.1002/chem.201500068. Epub 2015 May 26.

Solid-Phase Parallel Synthesis of Functionalised Medium-to-Large Cyclic Peptidomimetics through Three-Component Coupling Driven by Aziridine Aldehyde Dimers.

Author information

1
Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, 3001, 12e av nord Sherbrooke (QC) J1H 5N4 (Canada).
2
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto (ON) M5S 3H6 (Canada).
3
Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, 3001, 12e av nord Sherbrooke (QC) J1H 5N4 (Canada). eric.marsault@usherbrooke.ca.

Abstract

The first solid-phase parallel synthesis of macrocyclic peptides using three-component coupling driven by aziridine aldehyde dimers is described. The method supports the synthesis of 9- to 18-membered aziridine-containing macrocycles, which are then functionalized by nucleophilic opening of the aziridine ring. This constitutes a robust approach for the rapid parallel synthesis of macrocyclic peptides.

KEYWORDS:

drug discovery; macrocycles; peptides; small ring systems; solid-phase synthesis

PMID:
26014974
DOI:
10.1002/chem.201500068

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