Synthesis of hydrazinopeptides using solid-phase N-electrophilic amination: extension to the Fmoc/tert-butyl strategy and chemistry of the N-N bond in strong acid media.
The synthesis of hydrazinopeptides using solid-phase N-electrophilic amination was extended to the Fmoc/tert-butyl strategy. Both Boc/benzyl and Fmoc/tert-butyl strategies led to the isolation of by-products arising from the partial instability of the N-N bond during the final cleavage and deprotection step. Two paths of decomposition have been shown: the cleavage of the N-N bond leading to the regeneration of the amine and a Hofmann-type elimination yielding original dianisyl adducts. Our data suggest that the Fmoc/tert-butyl strategy is better suited for the synthesis of hydrazinopeptides.
Bonnet
D
D
Institut Pasteur de Lille/Institut de Biologie de Lille, France.
Samson
F
F
Rommens
C
C
Gras-Masse
H
H
Melnyk
O
O
D000143:Acids; D000586:Amination; D000595:Amino Acid Sequence; D005449:Fluorenes / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry*; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D010452:Peptide Biosynthesis
D000143:Acids; D005449:Fluorenes; D006834:Hydrazines