C-linked galactosyl serine AFGP analogues as potent recrystallization inhibitors.
[reaction: see text] A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.
Liu
Suhuai
S
Department of Chemistry, University of Ottawa, Ottawa, ON, Canada K1N6N5.
Ben
Robert N
RN
D021301:Antifreeze Proteins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D003460:Crystallization; D005690:Galactose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D021301:Antifreeze Proteins; D012694:Serine; D005690:Galactose