title: Cationic charged helical glycopolypeptide using ring opening polymerization of 6-deoxy-6-azido-glyco-N-carboxyanhydride.
abstract: 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.
authors.affiliation: CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road, Pune-411 008, India.
authors.forename: Ashif Y
authors.initials: AY
authors.lastname: Shaikh
authors.forename: Soumen
authors.initials: S
authors.lastname: Das
authors.forename: Debasis
authors.initials: D
authors.lastname: Pati
authors.forename: Vinita
authors.initials: V
authors.lastname: Dhaware
authors.forename: Sayam
authors.initials: S
authors.lastname: Sen Gupta
authors.forename: Srinivas
authors.initials: S
authors.lastname: Hotha
mesh_terms: D000588:Amines / Q000737:chemistry; D001386:Azides / Q000008:administration & dosage / Q000737:chemistry*; D001672:Biocompatible Materials / Q000008:administration & dosage / Q000737:chemistry; D002412:Cations / Q000008:administration & dosage / Q000737:chemistry*; D045744:Cell Line, Tumor; D005947:Glucose / Q000737:chemistry; D006020:Glycopeptides / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D008968:Molecular Conformation; D008970:Molecular Weight; D058105:Polymerization; D011108:Polymers / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D000588:Amines; D001386:Azides; D001672:Biocompatible Materials; D002412:Cations; D006020:Glycopeptides; D011108:Polymers; D014867:Water; D005947:Glucose