期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 9, 期 -, 页码 56-63出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.7
关键词
click chemistry; glycans; peptoids; polyalkynes; polyamines; solid-phase chemistry
资金
- Landesgraduiertenprogramm Baden-Wurttemberg
- Carl-Zeiss foundation
- Theodor Laymann Foundation
- Fonds der Chemischen Industrie
- SFB 645 [Z1]
- Helmholtz Program Biointerface
- Center for Functionalized Nanostructures (CFN), Karlsruhe
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 azido-sugars 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.
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