Postsynthetic functionalization of glycodendrons at the focal point

• Thisbe K. Lindhorst and
• Katharina Elsner

Beilstein J. Org. Chem. 2014, 10, 1482–1487, doi:10.3762/bjoc.10.152

• Thisbe K. Lindhorst Katharina Elsner Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3–4, D-24098 Kiel 10.3762/bjoc.10.152 Abstract Glycodendrons are multivalent glycoconjugates bearing an orthogonal functional group at the focal point of the

• molecule. This allows for their postsynthetic elaboration to achieve amphiphilic glycolipid mimetics, for example, which eventually can be applied in biology, biophysics, or material science. Here, postsynthetic modification of di- and tetravalent polyether glycodendrons has been explored using

• etherification, thiol-ene reaction and in particular olefin cross metathesis. Keywords: amphiphilic glycomimetics; cross metathesis; glycodendrons; multivalent glycoconjugates; multivalent glycosystems; Introduction In addition to nucleic acids and proteins, molecular life is based on a third important class

Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM₃-lactone mimetic

• Renato Ribeiro-Viana,
• Elena Bonechi,
• Javier Rojo,
• Clara Ballerini,
• Giuseppina Comito,
• Barbara Richichi and
• Cristina Nativi

Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

• biological properties of the monovalent synthetic antigen as an immunomodulator as well as an anti-adhesive agent in melanoma progression. Taking into account all these data and relying on recent results on the use of mannose-based glycodendrons as vectors for antigen delivery to DCs [34], we report here on

• kind of compounds based on multivalent ditopic glycodendrons might be used to address the preparation of a synthetic vaccine against melanoma. In addition, this strategy might be applied to other diseases in immunotherapy. Experimental Reagents were purchased from Sigma–Aldrich and Fluka and were used

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

• Daniel Fürniss,
• Timo Mack,
• Frank Hahn,
• Sidonie B. L. Vollrath,
• Katarzyna Koroniak,
• Ute Schepers and
• Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

• secondary structures [43]. CuAAC reactions for the attachment of sugar residues to peptoid backbones have been reported for some cases [44][45]; however, a fully glycosylated structure is unknown (for glycodendrons see [46]). In this study, we describe the first solid-phase synthesis of glycosylated