title: Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores.
abstract: Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed azide-alkyne cycloadditions. Evaluation of these compounds as α-mannosidase inhibitors led to significant multivalent effects and further demonstrated the decisive influence of scaffold rigidity on binding affinity enhancements.
authors.affiliation: Laboratoire de Synthèse Organique et Molécules Bioactives (SYBIO), Université de Strasbourg/CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg, France.
authors.forename: Mathieu L
authors.initials: ML
authors.lastname: Lepage
authors.affiliation: Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 132, I-84084 Fisciano Salerno, Italy.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Meli
authors.affiliation: Laboratoire de Synthèse Organique et Molécules Bioactives (SYBIO), Université de Strasbourg/CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg, France.
authors.forename: Anne
authors.initials: A
authors.lastname: Bodlenner
authors.affiliation: Université de Haute Alsace, Laboratoire de Chimie Organique et Bioorganique, EA4466, ENSCMu, 3, rue Alfred Werner, 68093 Mulhouse Cedex, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Tarnus
authors.affiliation: Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 132, I-84084 Fisciano Salerno, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: De Riccardis
authors.affiliation: Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 132, I-84084 Fisciano Salerno, Italy.
authors.forename: Irene
authors.initials: I
authors.lastname: Izzo
authors.affiliation: Laboratoire de Synthèse Organique et Molécules Bioactives (SYBIO), Université de Strasbourg/CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg, France ; Institut Universitaire de France, 103 Bd Saint-Michel, 75005 Paris, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Compain
keywords: cyclopeptoids; glycosidases; iminosugars; inhibitors; multivalency; mutivalent glycosystems