title: Synthesis of hexyl α-glucoside and α-polyglucosides by a novel Microbacterium isolate.
abstract: 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.
authors.affiliation: Department of Biochemical Engineering and Biotechnology, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
authors.forename: Swati
authors.initials: S
authors.lastname: Ojha
authors.forename: Saroj
authors.initials: S
authors.lastname: Mishra
authors.forename: Sumeet
authors.initials: S
authors.lastname: Kapoor
authors.forename: Subhash
authors.initials: S
authors.lastname: Chand
mesh_terms: D000192:Actinomycetales / Q000145:classification / Q000201:enzymology* / Q000302:isolation & purification / Q000378:metabolism*; D016000:Cluster Analysis; D004269:DNA, Bacterial / Q000737:chemistry / Q000235:genetics; D004275:DNA, Ribosomal / Q000737:chemistry / Q000235:genetics; D004800:Enzymes, Immobilized / Q000378:metabolism*; D005960:Glucosides / Q000737:chemistry / Q000378:metabolism*; D000441:Hexanols / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000378:metabolism; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D010802:Phylogeny; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D017422:Sequence Analysis, DNA; D000520:alpha-Glucosidases / Q000378:metabolism*
chemical_list: D004269:DNA, Bacterial; D004275:DNA, Ribosomal; D004800:Enzymes, Immobilized; D005960:Glucosides; D000441:Hexanols; D012336:RNA, Ribosomal, 16S; D008320:Maltose; D000520:alpha-Glucosidases