Publikationsdatum:
2014-06-18
Beschreibung:
Oligoglycines designed in a star-like fashion, so-called tri- and tetraantennary molecules, were found to form highly ordered supramers in aqueous medium. The formation of these supramers occurred either spontaneously or due to the assistance of a mica surface. The driving force of the supramer formation is hydrogen bonding, the polypeptide chain conformation is related to the folding of helical polyglycine II (PG II). Tri- and tetraantennary molecules are capable of association if the antenna length reach 7 glycine (Gly) residues. Properties of similar biantennary molecules have not been investigated yet, and we compared their self-aggregating potency with similar tri- and tetraantennary analogs. Here, we synthesized oligoglycines of the general formula R-Gly n -Х-Gly n -R (X = -HN-(СН 2 ) m -NH-, m = 2, 4, 10; n = 1–7) without pendant ligands (R = H) and with two pendant sialoligands (R = sialic acid or sialooligosaccharide). Biantennary oligoglycines formed PG II aggregates, their properties, however, differ from those of the corresponding tri- and tetraantennary oligoglycines. In particular, the tendency to aggregate starts from Gly 4 motifs instead of Gly 7 . The antiviral activity of end-glycosylated peptides was studied, and all capable of assembling glycopeptides demonstrated an antiviral potency which was up to 50 times higher than the activity of peptide-free glycans. Beilstein J. Org. Chem. 2014, 10, 1372–1382. doi:10.3762/bjoc.10.140
Schlagwort(e):
glycopeptidesinfluenza virusmultivalent glycosystemsoligoglycinepolyglycine IIself-assemblingtectomers
Digitale ISSN:
1860-5397
Thema:
Chemie und Pharmazie
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