Synthesis of p-nitrophenyl 6(5)-O-benzyl-alpha-maltopentaoside, a substrate for alpha amylases.
p-Nitrophenyl alpha-maltopentaoside, having a benzyl group on O-6 of the terminal (nonreducing) D-glucosyl group was prepared by use of a reductive ring-opening reaction. Highly regioselective reduction of p-nitrophenyl O-(2,3-di-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranosyl)-(1----4)- tris[O-(2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl)-(1----4)]-2,3,6-tri- O- benzoyl-alpha-D-glucopyranoside by dimethylamine-borane and p-toluenesulfonic acid, followed by debenzoylation, gave p-nitrophenyl O-(6-O-benzyl-alpha-D-glucopyranosyl)-(1----4)-tris[O-alpha-D-glucopyran osyl- (1----4)]-alpha-D-glucopyranoside. An experiment was done on the mode of action of human pancreatic and salivary alpha amylases on this derivative. The compound is suitable as a substrate for the assay of alpha amylase when used with glucoamylase and alpha-D-glucosidase as coupling enzymes.
Satomura
S
S
Osaka Research Division, Wako Pure Chemical Industries, Ltd., Hyogo, Japan.
Iwata
T
T
Sakata
Y
Y
Omichi
K
K
Ikenaka
T
T
D002236:Carbohydrate Conformation; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D006027:Glycosides / Q000138:chemical synthesis*; D006801:Humans; D007202:Indicators and Reagents; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010179:Pancreas / Q000201:enzymology; D012463:Saliva / Q000378:metabolism; D013379:Substrate Specificity; D000516:alpha-Amylases / Q000097:blood / Q000378:metabolism*
D006027:Glycosides; D007202:Indicators and Reagents; D009844:Oligosaccharides; C056544:4-nitrophenyl-O-(6-O-benzyl)-glucopyranosyl(1--4)-O-glucopyranosyl(1--4)-O-glucopyranosyl(1--4)-O-glucopyranosyl(1--4)-glucopyranoside; D000516:alpha-Amylases