Second generation C-linked AFGP analogues : Tailoring recrystallization-inhibition and thermal hysteresis properties

ORGN 794

Vincent R. Bouvet1, Anastasia V. Murphy2, Matthew F. L. Parker3, and Robert N. Ben1. (1) Department of Chemistry, Univertsity of Ottawa, Pavillon D'Iorio 10 Marie Curie, Ottawa, ON K1N 6N5, Canada, (2) Chemistry, State University Of New York at Binghamton, Vestal Pkwy East, Binghamton, NY 13902, (3) Department of Chemisty, Institute for Materials Research, and Center for Research on Environmental Systems, State University of New York, Vestal Parkway East, Binghamton, NY 13902
During the past decade, antifreeze glycoproteins have exhibited tremendous potential for many industrial, commercial and medical applications. However, their potency as recrystallization-inhibitors is limited by their thermal hysteresis activity and their ability to modify the habit of ice crystals such that cellular damage is maximized. After our recent report that C-linked antifreeze analogues exhibit minimal TH activity but potent recrystallization-inhibition, we sought to increase the efficacy of these compounds for cryopreservation applications. In an effort to better understand the structural requirements for recrystallization-inhibition activity and facilitate the rational design of new marketable analogues, a series of second-generation C-linked AFGP analogues have been prepared and evaluated for antifreeze protein-specific activity.