Efficient synthesis of C-terminal modified peptide ketones for chemical ligations

Synthesis of a C-terminal modified peptide with an α-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 f...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2005-12, Vol.15 (24), p.5442-5445
Main Authors: Marceau, Philippe, Buré, Corinne, Delmas, Agnès F.
Format: Article
Language:English
Subjects:
Amino Acid Sequence
C-terminal modified peptide
Chemistry
Exact sciences and technology
Hydrogen-Ion Concentration
Indicators and Reagents
Ketone
Ketones - chemical synthesis
Kinetics
Ligands
Models, Molecular
Molecular Conformation
Molecular Sequence Data
Organic chemistry
Oxime ligation
Peptides
Peptides - chemical synthesis
Piperidines
Preparations and properties
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Summary:Synthesis of a C-terminal modified peptide with an α-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 5 h at pH 2.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.08.105