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![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A novel route towards cycle-tail peptides using oxime resin: teaching an old dog a new trick
Christopher Bérubé1, Alexandre Borgia, Normand Voyer
1Département de Chimie and PROTEO, Université Laval, Pavillon Alexandre-Vachon, Faculté des sciences et de génie, 1045 avenue de la Médecine, Québec, QC, CanadaG1V 0A6. normand.voyer@chm.ulaval.ca.
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.
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