02236nas a2200205 4500008004100000022001400041245012400055210006900179260007100248300001400319490000700333520144600340100002201786700001601808700001801824700002001842700002201862700002001884856012601904 2014 eng d a1525-779700aCationic charged helical glycopolypeptide using ring opening polymerization of 6-deoxy-6-azido-glyco-N-carboxyanhydride0 aCationic charged helical glycopolypeptide using ring opening pol a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcOCT a3679-36860 v153 a
Glycopolypeptides with a defined secondary structure are of significance in understanding biological phenomena. Synthetic glycopolypeptides, or polypeptides featuring pendant carbohydrate moieties, have been of particular interest in the field of tissue engineering and drug delivery. In this work, we have synthesized charged water-soluble glycopolypeptides that adopt a helical conformation in water. This was carried out by the synthesis of a glyco-N-carboxyanhydride (glyco-NCA) containing an azide group at the sixth position of the carbohydrate ring. Subsequently, the NCA was polymerized to obtain azide-containing glycopolypeptides having good control over molecular weight and polydispersity index (PDI) in high yields. We were also able to control the incorporation of the azide group by synthesizing random co-glycopolypeptide containing 6-deoxy-6-azido and regular 6-OAc functionalized glucose. This azide functionality allows for the easy attachment of a bioactive group, which could potentially enhance the biological activity of the glycopolypeptide. We were able to obtain water-soluble charged glycopolypeptides by both reducing the azide groups into amines and using CuAAC with propargylamine. These charged glycopolypeptides were shown to have a helical conformation in water. Preliminary studies showed that these charged glycopolypeptides showed good biocompatibility and were efficiently taken up by HepG2 cells.
1 aShaikh, Ashif, Y.1 aDas, Soumen1 aPati, Debasis1 aDhaware, Vinita1 aGupta, Sayam, Sen1 aHotha, Srinivas uhttp://library.ncl.res.in/content/cationic-charged-helical-glycopolypeptide-using-ring-opening-polymerization-6-deoxy-6-0