title: 9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis.
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.
authors.affiliation: Centre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montreal, P.O. Box 6128, Station Downtown, Montreal, Québec, H3C 3J7, Canada.
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Aspin
authors.affiliation: Centre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montreal, P.O. Box 6128, Station Downtown, Montreal, Québec, H3C 3J7, Canada.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Taillemaud
authors.affiliation: Centre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montreal, P.O. Box 6128, Station Downtown, Montreal, Québec, H3C 3J7, Canada.
authors.forename: Patrick
authors.initials: P
authors.lastname: Cyr
authors.affiliation: Centre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montreal, P.O. Box 6128, Station Downtown, Montreal, Québec, H3C 3J7, Canada. andre.charette@umontreal.ca.
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D002712:Chlorides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D017646:Organosilicon Compounds / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002712:Chlorides; D017646:Organosilicon Compounds; D010455:Peptides
keywords: amides; amino acids; peptides; silanes; synthetic methods