Authors
Chantelle J Capicciotti, John F Trant, Mathieu Leclere, Robert N Ben
Publication date
2011/4/20
Journal
Bioconjugate Chemistry
Volume
22
Issue
4
Pages
605-616
Publisher
American Chemical Society
Description
C-Linked antifreeze glycoprotein (C-AFGP) analogues have been shown to have potent ice recrystallization inhibition (IRI) activity. However, the lengthy synthesis of these compounds is not amenable to large-scale preparation for the many commercial, industrial, and medical applications that exist. This paper describes the synthesis of triazole-containing AFGPs using a convergent solid-phase synthesis (SPS) approach in which multiple carbohydrate derivatives are coupled to a resin-bound synthetic peptide in a single step. Modified “Click” conditions using dry DMF as solvent with catalytic Cu(II), sodium ascorbate, and microwave radiation afforded the synthesis of AFGP analogues 912 in 16−54% isolated yield. Compound 9 demonstrated no IRI activity, while compounds 10, 11, and 12 were moderate inhibitors of ice recrystallization. These results suggest that, while the triazole group is a structural mimetic of …
Total citations
201120122013201420152016201720182019202020212022202315551034322413