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Cationic charged helical glycopolypeptide using ring opening polymerization of 6-deoxy-6-azido-glyco-N-carboxyanhydride.
- Source :
-
Biomacromolecules [Biomacromolecules] 2014 Oct 13; Vol. 15 (10), pp. 3679-86. Date of Electronic Publication: 2014 Sep 02. - Publication Year :
- 2014
-
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.
- Subjects :
- Amines chemistry
Azides administration & dosage
Biocompatible Materials administration & dosage
Biocompatible Materials chemistry
Cations administration & dosage
Cell Line, Tumor
Glucose chemistry
Glycopeptides administration & dosage
Hep G2 Cells
Humans
Molecular Conformation
Molecular Weight
Polymerization
Polymers chemistry
Water chemistry
Azides chemistry
Cations chemistry
Glycopeptides chemical synthesis
Glycopeptides chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1526-4602
- Volume :
- 15
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- Biomacromolecules
- Publication Type :
- Academic Journal
- Accession number :
- 25122513
- Full Text :
- https://doi.org/10.1021/bm5009537