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

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 form...

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Published in:Beilstein journal of organic chemistry 2014-06, Vol.10 (1), p.1372-1382
Main Authors: Tsygankova, Svetlana V, Chinarev, Alexander A, Tuzikov, Alexander B, Severin, Nikolai, Kalachev, Alexey A, Rabe, Juergen P, Gambaryan, Alexandra S, Bovin, Nicolai V
Format: Article
Language:English
Subjects:
Chemistry
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glycopeptides
influenza virus
multivalent glycosystems
oligoglycine
polyglycine II
self-assembling
tectomers
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Summary: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-(СН2) 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 Gly4 motifs instead of Gly7. 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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.10.140