Structurally diverse disaccharide analogs of antifreeze glycoproteins and their ability to inhibit ice recrystallization

Anna K. Balcerzak, University of Ottawa
Sandra S. Ferreira, University of Ottawa
John F. Trant, University of Ottawa
Robert N. Ben, University of Ottawa


The β-D-galactosyl-(1,3)-α-N-acetyl-D-galactosamine disaccharide is present in antifreeze glycoproteins (AFGPs). Analogs of this disaccharide including the β-linked (1,3)-, (1,4)-, and (1,6)-galactosyl-N-acetyl galactosamine and the β-(1,3)-galactosyl-galactoside were synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The results from this study demonstrate that the b-linked-(1,4) disaccharide exhibits more potent IRI activity than the native b-linked-(1,3) disaccharide. The C2 N-acetyl group of the disaccharide does not affect IRI activity but in monosaccharides, the presence of the C2 N-acetyl group decreases IRI activity. The current study will facilitate the design of potent small-molecule ice recrystallization inhibitors. © 2011 Elsevier Ltd. All rights reserved.