Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization

• Published in: Bioorganic & medicinal chemistry letters 2010-09, Vol.20 (17), p.5251-5254
• Main Authors: Chaytor, Jennifer L., Ben, Robert N.
• Format: Article
• Language: English
• Subjects: AFGP 8; Anesthesia. Intensive care medicine. Transfusions. Cell therapy and gene therapy; Antifreeze glycoprotein; Antifreeze Proteins - chemistry; Antifreeze Proteins - pharmacology; Biological and medical sciences; Carbohydrate hydration; Carbohydrates - pharmacology; Clinical death. Palliative care. Organ gift and preservation; Crystallization; Fluorine; Fluorine - chemistry; Ice; Ice recrystallization inhibition; Medical sciences
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2010.06.148

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.