Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

• Main Authors: Daniel Fürniss, Timo Mack, Frank Hahn, Sidonie B. L. Vollrath, Katarzyna Koroniak, Ute Schepers, Stefan Bräse
• Format: Article
• Language: English
• Published: Beilstein-Institut 2013-01-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: click chemistry; glycans; peptoids; polyalkynes; polyamines; solid-phase chemistry
• Online Access: https://doi.org/10.3762/bjoc.9.7

Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six alkyne groups, the latter were modified with azidosugar building blocks by using copper-catalyzed azide alkyne cycloadditions. In addition, the up-scaling of some particular azide-modified sugars is described.