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Issue 47, 2018
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A novel route towards cycle-tail peptides using oxime resin: teaching an old dog a new trick

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Abstract

Two anabaenopeptins, Schizopeptin 791 and anabaenopeptin NZ825, have similar structural features and have been synthesized via a novel acid-catalyzed head-to-side-chain concomitant cyclization/cleavage reaction on oxime resin. The methodology gave rapid access to the anabaenopeptin scaffold by taking advantage of a combined solid-phase/solution-phase synthetic strategy. Also, as side-products of the synthesis, large C2-symmetric 38-member cyclic peptides ring bearing two endocyclic lysine side-chains were isolated, constituting a novel cyclic peptide scaffold.

Graphical abstract: A novel route towards cycle-tail peptides using oxime resin: teaching an old dog a new trick

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Publication details

The article was received on 01 Aug 2018, accepted on 24 Sep 2018 and first published on 25 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB01868E
Citation: Org. Biomol. Chem., 2018,16, 9117-9123
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    A novel route towards cycle-tail peptides using oxime resin: teaching an old dog a new trick

    C. Bérubé, A. Borgia and N. Voyer, Org. Biomol. Chem., 2018, 16, 9117
    DOI: 10.1039/C8OB01868E

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