9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis

A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy‐to‐access 9‐silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino aci...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-10, Vol.55 (44), p.13833-13837
Main Authors: Aspin, Samuel J., Taillemaud, Sylvain, Cyr, Patrick, Charette, André B.
Format: Article
Language:English
Subjects:
Amides
Amino acids
Chemical bonds
Chlorides - chemistry
Coupling agents
Crystallography, X-Ray
Dichlorides
Models, Molecular
Molecular Conformation
Organosilicon Compounds - chemistry
Peptide synthesis
Peptides
Peptides - chemical synthesis
Peptides - chemistry
silanes
Synthesis
synthetic methods
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Summary:A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy‐to‐access 9‐silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing the two coupling partners together before being subsequently eliminated. The desired amides or peptide bonds are thus furnished in good yields and with low to no epimerization. A chemical ligation mechanism was proposed for amide bond formation with 9‐silafluorenyl dichlorides as new coupling reagents. This approach enabled the synthesis of peptides in a simple and unprecedented manner without preactivation of either the carboxylic acid or amine termini of the amino acids.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201606120