Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

• Svetlana V. Tsygankova,
• Alexander A. Chinarev,
• Alexander B. Tuzikov,
• Nikolai Severin,
• Alexey A. Kalachev,
• Juergen P. Rabe,
• Alexandra S. Gambaryan and
• Nicolai V. Bovin

Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

• assembling glycopeptides demonstrated an antiviral potency which was up to 50 times higher than the activity of peptide-free glycans. Keywords: glycopeptides; influenza virus; multivalent glycosystems; oligoglycine; polyglycine II; self-assembling; tectomers; Introduction Recently, we have synthesized and

• ]. Results and Discussion Synthesis of biantennary oligoglycines and their glyco derivatives The synthesized biantennary oligoglycines and their glyco derivatives are presented in Figure 1. Analogously to tri- and tetraantennary molecules, oligoglycine antennas are connected according to the ‘head-to-head

• ’ principle, i.e., by their C-termini, so that the two amino groups are terminal. The obtained compounds differ threefold. Firstly, they differ by core X nature: hydrophilic oligoethylene glycol (OEG), hydrophobic flexible decamethylene (C10), or short ethylene (C2). Secondly, the length of oligoglycine

A bivalent glycopeptide to target two putative carbohydrate binding sites on FimH

• Thisbe K. Lindhorst,
• Kathrin Bruegge,
• Andreas Fuchs and
• Oliver Sperling

Beilstein J. Org. Chem. 2010, 6, 801–809, doi:10.3762/bjoc.6.90

• mannotrioside. Hence, a monomeric mannoside and the trisaccharide α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man were selected as carbohydrate ligands and azidoethyl aglycone moieties were chosen to allow their ligation via an oligoglycine spacer of an appropriate length. The well-known squaric acid diester linkage