Chemo-enzymatic synthesis of galactosylmaltooligosaccharidonolactone as a substrate analogue inhibitor for mammalian alpha-amylase

Journal of Biochemistry
M TakadaT Usui

Abstract

We performed chemo-enzymatic transformation of maltooligosaccharides into both end-modified oligosaccharidonolactones of potential use as substrate analogue inhibitors for mammalian alpha-amylases. Enzymatic modification of the non-reducing end glucosyl residue of the maltooligosaccharide was first performed by transglycosylation with beta-D-galactosidase from Bacillus circulans. When maltotriose and maltotetraose were the acceptors, the enzyme regioselectively synthesized 4(3)-O-beta-D-galactosyl maltotriose (LG3) and 4(4)-O-beta-D-galactosyl maltotetraose (LG4) from lactose as a donor. LG4 was further selectively hydrolyzed with a specific alpha-amylase to afford 4(2)-O-beta-D-galactosyl maltose (LG2). The anomer hydroxyl groups of LG2 and LG3 were chemically oxidized to give the corresponding lactones, 4(2)-O-beta-D-galactosyl maltobionolactone (LG2O) and 4(3)-O-beta-D-galactosyl maltotrionolactone (LG3O), respectively. LG2O and LG3O, which are competitive inhibitors for mammalian alpha-amylases, exhibited Ki values of the order of 2.8-18.0 microM, with p-nitrophenyl alpha-maltopentaoside (G5P) as the substrate. On 1H-NMR analysis, these oligosaccharidonolactones were shown to be transformed into the corresponding aldonic ac...Continue Reading

Citations

Aug 12, 2004·The Journal of Biological Chemistry·Shin NumaoStephen G Withers

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