Synthesis of hexyl α-glucoside and α-polyglucosides by a novel Microbacterium isolate

Alkyl-glucosides and alkyl-polyglucosides are the new-generation biodegradable surfactants with good emulsifying and wetting properties. The α-forms of these glucosides occur in antibiotics and also stimulate nasal absorption of many drugs. In this paper, we report the synthesis of hexyl α-glucoside and α-polyglucosides using cell-bound α-glucosidase activity of a novel strain of Microbacterium paraoxydans. A number of cell-bound glycosyl hydrolase activities were detected in the isolate with the maximum hydrolytic activity of 180 IU g(-1) dry wt cells on p-nitrophenyl-α-D-glucopyranoside. In a micro-aqueous system, at a water activity of 0.69, 1.8 g l(-1) of hexyl α-glucoside (corresponding to about 25 % yield) was synthesized by whole cells with maltose and hexanol as substrates. The concentration was enhanced to 11 g l(-1) (~60 % yield) in a biphasic system at a water content of 60 %. (1)H and (13)C NMR spectra of the purified compound confirmed the synthesized product to be hexyl-α-D-glucopyranoside, while the presence of hexyl di- and tri-glucosides was confirmed by electrospray ionization mass spectrometry. The cell-driven synthesis makes this an extremely attractive alternative for synthesis of such compounds.