Artificial glycopolypeptide conjugates: simple synthesis of lactose- and N,N'-diacetylchitobiose-substituted poly(L-glutamic acid)s through N-beta-glycoside linkages and their interaction with lectins.
Poly(glutamic acid)s carrying lactose- and N,N'-diacetylchitobiose residues were synthesized via a simple two-step procedure. The oligosaccharides were treated with ammonium hydrogen carbonate and the resulting N-beta-glycosylamine was coupled with pendant carboxyl groups of poly(L-glutamic acid) in the presence of a mixture of benzotriazol-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and 1-hydroxybenzotriazole (HOBt) in dimethyl sulfoxide. The oligosaccharide incorporated as pendant N-glycosides was estimated by 1H-NMR spectroscopy to be 30 mol% (or 45 wt%) for lactose and 27 mol% (46 wt%) for chitobiose. The glycopolypeptide carrying N,N'-diacetyl-chitobiose inhibited hemagglutination activity of wheat germ agglutinin (WGA) much more strongly (about 10(6) times) than N,N'-diacetylchitobiose itself. The high activity is due to the cluster or high density effect of the glycopolypeptides.
Kobayashi
K
K
Graduate School of Engineering, Nagoya University, Chikusa, Japan. kobayash@apchem.nagoya-u.ac.jp
Tawada
E
E
Akaike
T
T
Usui
T
T
D006020:Glycopeptides / Q000138:chemical synthesis* / Q000378:metabolism; D006384:Hemagglutination; D006801:Humans; D007785:Lactose; D037102:Lectins / Q000378:metabolism*; D011099:Polyglutamic Acid / Q000138:chemical synthesis* / Q000378:metabolism
D006020:Glycopeptides; D037102:Lectins; D011099:Polyglutamic Acid; D007785:Lactose