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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (10), p. 1406-1412, 2014

DOI: 10.3762/bjoc.10.144

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Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

Journal article published in 2014 by Mathieu Louis Lepage, Alessandra Meli ORCID, Anne Bodlenner, Céline Tarnus, Francesco De Riccardis ORCID, Irene Izzo ORCID, Philippe Compain
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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.