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


ABSTRACT: Cyclic N-propargyl ?-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 ?-mannosidase inhibitors led to significant multivalent effects and further demonstrated the decisive influence of scaffold rigidity on binding affinity enhancements.

SUBMITTER: Lepage ML 

PROVIDER: S-EPMC4077385 | biostudies-other | 2014

REPOSITORIES: biostudies-other

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

Lepage Mathieu L ML   Meli Alessandra A   Bodlenner Anne A   Tarnus Céline C   De Riccardis Francesco F   Izzo Irene I   Compain Philippe P  

Beilstein journal of organic chemistry 20140623


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 bin  ...[more]

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