Synthesis of chromogenic substrates of α-amylases on a cyclodextrin basis

• Published in: Carbohydrate research 1997-10, Vol.303 (4), p.407-415
• Main Authors: Farkas, Erzsébet, Jánossy, Lóránt, Harangi, János, Kandra, Lili, Lipták, András
• Format: Article
• Language: English
• Subjects: Acetolysis; Acetylation; alpha-Amylases - metabolism; Carbohydrate Sequence; Chromatography, High Pressure Liquid; Crystallization; Cyclodextrins; Cyclodextrins - metabolism; Humans; Maltooligosaccharide derivatives; Models, Chemical; Molecular Sequence Data; Pancreas - enzymology; Toluene; α-Amylase substrate
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(97)00187-0

One-pot acetylation and subsequent partial acetolysis of α-, β- and γ-cyclodextrins resulted in crystalline peracetylated malto-hexaose, -heptaose, and -octaose, respectively. Prolonged acetolysis of β-cyclodextrin gave a mixture of acetylated maltooligosaccharides, from which peracetylated malto-triose, -tetraose, and -pentaose were isolated. The acetylated oligosaccharides were converted into α-acetobromo derivatives, and then transformed into 4-nitrophenyl and 2-chloro-4-nitrophenyl β-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 α-amylase. One-pot acetylation and subsequent partial acetolysis of cyclodextrins resulted in the peracetylated maltooligomers (dp 3–8), which were transformed into 4-nitrophenyl and 2-chloro-4-nitrophenyl β-glycosides, the 4.6- O-benzylidene derivatives of NP-glycosides were also prepared