Synthesis of C6-amino agarose and evaluation of its antibacterial activity

Abstract

In this paper, the biologically inert agarose was selectively modified at C6 of β-d-Galp units to produce an amino derivative with antibacterial property. The synthetic route involved the preparation of tosyl and azido agarose intermediates. All the polysaccharide derivatives were characterized by mono- and bidimensional ¹H and ¹³C NMR and FT-IR analysis. A water-soluble amino polymer (M_w = 39,000 g mol^-1, DS_amino = 0.50) was produced by partial acid hydrolysis showing bactericidal and bacteriostatic activity against P. aeruginosa (ATCC 9027), S. aureus (ATCC 6538), and E. coli (ATCC 25922), with MIC values lower than 2.5 mg mL^-1 and MBC values ranging from 2.5 to 5.0 mg mL^-1.

Keywords: Agarose; Amino polysaccharide; Antibacterial activity; Azido polysaccharide; Galactan; Tosylation.