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Glycobiology, 2002, Vol. 12, No. 4 283-290
© 2002 Oxford University Press

Synthesis and characterization of a novel glycopolymer with protective activity toward human anti-{alpha}-Gal antibodies

Amedeo Vetere1, Ivan Donati, Cristiana Campa, Sabrina Semeraro, Amelia Gamini and Sergio Paoletti

Department of Biochemistry, Biophysics and Macromolecular Chemistry, University of Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy

An efficient and rapid synthesis of the derivative of the biocompatible polymer poly(styrene co-maleic acid) with Linear B disaccharide (Galili antigen) was achieved. The oligosaccharide portion was obtained by a transglycosylation reaction catalyzed by coffee bean {alpha}-D-galactosidase using p-nitrophenyl-{alpha}-D-galactopyranoside both as donor and as acceptor. The reaction was carried out in aqueous buffer without any organic cosolvent. The molar yield (30%) and the regioselectivity (82%) were significantly improved with respect to the data so far reported in the literature. The selective reduction of the p-nitrophenyl group afforded the p-aminophenyl derivative of Linear B disaccharide. Linkage of this derivative via an amidic bond to the poly(styrene co-maleic acid) was obtained by using N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and N-hydroxysuccinimide. The products were chemically characterized by ionspray mass spectrometry, infrared, 13C- and 1H-nuclear magnetic resonance. The glycopolymer specifically reacts with human serum containing antibodies and with a mixture of partially purified human IgG and IgM anti-Linear B. It efficiently protects pig kidney PK15 cells from cytotoxic effects of human serum.

1 To whom correspondence should be addressed


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