title: Structurally diverse disaccharide analogs of antifreeze glycoproteins and their ability to inhibit ice recrystallization.
abstract: 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 β-linked-(1,4) disaccharide exhibits more potent IRI activity than the native β-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.
authors.affiliation: Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada.
authors.forename: Anna K
authors.initials: AK
authors.lastname: Balcerzak
authors.forename: Sandra S
authors.initials: SS
authors.lastname: Ferreira
authors.forename: John F
authors.initials: JF
authors.lastname: Trant
authors.forename: Robert N
authors.initials: RN
authors.lastname: Ben
mesh_terms: D021301:Antifreeze Proteins / Q000737:chemistry*; D003460:Crystallization; D004187:Disaccharides / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D021301:Antifreeze Proteins; D004187:Disaccharides