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pubmed-article:10532233pubmed:abstractTextThe 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.lld:pubmed
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pubmed-article:10532233pubmed:articleTitleSynthesis 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.lld:pubmed
pubmed-article:10532233pubmed:affiliationInstitut Pasteur de Lille/Institut de Biologie de Lille, France.lld:pubmed
pubmed-article:10532233pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:10532233pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed