Premium
9‐Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis
Author(s) -
Aspin Samuel J.,
Taillemaud Sylvain,
Cyr Patrick,
Charette André B.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201606120
Subject(s) - chemistry , peptide bond , reagent , peptide , epimer , amine gas treating , combinatorial chemistry , stoichiometry , chemical ligation , peptide synthesis , coupling (piping) , carboxylic acid , organic chemistry , biochemistry , materials science , metallurgy
Abstract 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.