title: Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization.
abstract: A short fluorinated antifreeze glycopeptide (2) was synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The activity of 2 was compared to native biological antifreeze AFGP 8 and a rationally designed C-linked AFGP analogue (OGG-Gal, 1). In addition, a simple fluorinated galactose derivative was prepared and its IRI activity was compared to non-fluorinated compounds. The results from this study suggest that the stereochemistry at the anomeric position in the carbohydrate plays a role in imparting ice recrystallization inhibition activity and that incorporation of hydrophobic groups such as fluorine atoms cause a decrease in IRI activity. These observations are consistent with the theory that fluorine atoms increase ordering of bulk water resulting in a decrease of IRI activity, supporting our previously proposed mechanism of ice recrystallization inhibition.
authors.affiliation: Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada.
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Chaytor
authors.forename: Robert N
authors.initials: RN
authors.lastname: Ben
mesh_terms: D021301:Antifreeze Proteins / Q000737:chemistry / Q000494:pharmacology*; D002241:Carbohydrates / Q000494:pharmacology*; D003460:Crystallization; D005461:Fluorine / Q000737:chemistry*; D007053:Ice
chemical_list: D021301:Antifreeze Proteins; D002241:Carbohydrates; D007053:Ice; D005461:Fluorine