Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives》.pdf

Carbohydrate Polymers 136 (2016) 474–484 Contents lists available at ScienceDirect Carbohydrate Polymers j o u r na l h o me p a g e : w w w. elsev /locate/car bpol Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives Ruoran Zhang a , Shu Liu c , Kevin J. Edgar a,b,∗ a Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, VA 24061, United States b Department of Sustainable Biomaterials, College of Natural Resources and Environment, Virginia Tech, Blacksburg, VA 24061, United States c Department of Chemistry, College of Science, Virginia Tech, Blacksburg, VA 24061, United States a r t i c l e i n f o a b s t r a c t Article history: Curdlan, a bioactive -1,3-glucan, is of intense interest for pharmaceutical and biomedical applications. Received 27 April 2015 Cationic derivatives of curdlan and other polysaccharides are especially attractive for their potential Received in revised form 4 September 2015 to interact in controlled fashion with proteins, among many other possible applications, but rela- Accepted 5 September 2015 tively few methods exist for their synthesis. Herein we report a regioselective method for preparation Available online 8 September 2015 of cationic, water-soluble 6-(N,N,N-trialkylammonio)-6-deoxycurdlan salts by reaction of 6-bromo-6- deoxycurdlan and its 2,4-O-diesters with trialkylamines.