Highly swellable hydrogel of regioselectively aminated (1→3)-α-d-glucan crosslinked with ethylene glycol diglycidyl ether

Abstract

(1→3)-α-d-glucan synthesized by glucosyltransferase J (GtfJ) cloned from Streptococcus salivarius was regioselectively aminated as 6-amino-6-deoxy-(1→3)-α-d-glucan (aminoglucan) through three steps: bromination, azidation, and reduction. The degree of substitution of the amino group was determined by elemental analysis to be 0.97 and the molecular weight was 3.74×10⁴ as measured by size exclusion chromatography. The regioselective amination at the C6 position of every pyranose ring was confirmed by ¹H/¹³C NMR and solid state ¹⁵N cross polarization/magic angle spinning NMR spectroscopy. Aminoglucan was characterized by FT-IR, X-ray diffraction and thermogravimetric analysis. Solubility of aminoglucan in various solvents was investigated and confirmed in aqueous solution at pH ≤ 11. Therefore, aminoglucan was crosslinked with ethylene glycol diglycidyl ether (EGDE) by an epoxy-ring opening reaction under alkaline conditions. The obtained EGDE-crosslinked aminoglucan hydrogels were highly swellable in water owing to a strong water-holding ability and no water was released on compression and breaking of the gels.

Keywords: (1→3)-α-d-glucan; Amination; Glucosyltransferase; Hydrogel; Solubility; Streptococcus salivarius.