Synthesis of chromogenic substrates of alpha-amylases on a cyclodextrin basis.
One-pot acetylation and subsequent partial acetolysis of alpha-, beta- and gamma-cyclodextrins resulted in crystalline peracetylated malto-hexaose, -heptaose, and -octaose, respectively. Prolonged acetolysis of beta-cyclodextrin gave a mixture of acetylated maltooligosaccharides, from which peracetylated malto-triose, -tetraose, and -pentaose were isolated. The acetylated oligosaccharides were converted into alpha-acetobromo derivatives, and then transformed into 4-nitrophenyl and 2-chloro-4-nitrophenyl beta-glycosides. From the 4-nitrophenyl glycosides 4,6-O-benzylidene derivatives were prepared, which were used together with the free glycosides as substrates of porcine pancreatic alpha-amylase.
Farkas
E
E
Department of Biochemistry, Lajos Kossuth University, Debrecen, Hungary.
Jánossy
L
L
Harangi
J
J
Kandra
L
L
Lipták
A
A
D000107:Acetylation; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D003505:Cyclodextrins / Q000378:metabolism*; D006801:Humans; D008956:Models, Chemical; D008969:Molecular Sequence Data; D010179:Pancreas / Q000201:enzymology; D014050:Toluene; D000516:alpha-Amylases / Q000378:metabolism*
D003505:Cyclodextrins; D014050:Toluene; D000516:alpha-Amylases