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

作者：Chaytor Jennifer L; Ben Robert N^*

来源：Bioorganic & Medicinal Chemistry Letters, 2010, 20(17): 5251-5254.

DOI：10.1016/j.bmcl.2010.06.148

• Antifreeze glycoprotein
• AFGP 8
• Ice recrystallization inhibition
• Fluorine
• Carbohydrate hydration

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.

• 出版日期2010-9-1