Efficient synthesis of C-terminal modified peptide ketones for chemical ligations.
Synthesis of a C-terminal modified peptide with an alpha-amido methylketone was efficiently carried out using a backbone-amide-type linker loading with a monofunctionalized diamine, provided that no base such as piperidine or diisopropylethylamine or a reducing agent such as triisopopylsilane was used for the synthetic pathway. The ketoxime-forming chemoselective ligation between a methylketone and an aminooxy was quantitative in 5h at pH 2.
Marceau
Philippe
P
Centre de biophysique moléculaire, UPR 4301 CNRS , rue Charles Sadron, 45071 Orléans, Cedex 2, France.
Buré
Corinne
C
Delmas
Agnès F
AF
D000595:Amino Acid Sequence; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis*; D007700:Kinetics; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D010880:Piperidines
D007202:Indicators and Reagents; D007659:Ketones; D008024:Ligands; D010455:Peptides; D010880:Piperidines