title: 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.
abstract: 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.
authors.affiliation: Institut Pasteur de Lille/Institut de Biologie de Lille, France.
authors.forename: D
authors.initials: D
authors.lastname: Bonnet
authors.forename: F
authors.initials: F
authors.lastname: Samson
authors.forename: C
authors.initials: C
authors.lastname: Rommens
authors.forename: H
authors.initials: H
authors.lastname: Gras-Masse
authors.forename: O
authors.initials: O
authors.lastname: Melnyk
mesh_terms: 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
chemical_list: D000143:Acids; D005449:Fluorenes; D006834:Hydrazines