Carbohydrate Research p. 180 - 186 (1999)
Update date:2022-08-29
Topics:
Kandra, Lili
Gyemant, Gyoengyi
Liptak, Andras
In the present work, we aimed to develop a new chemoenzymatic procedure for the synthesis of β-maltooligosaccharide glycosides. The primer in the enzymatic reaction was 2-chloro-4-nitrophenyl β-maltoheptaoside (G7-CNP), which was synthesised from β-cyclodextrin (β-CD) using a very convenient chemical method [E. Farkas, L. Janossy, J. Harangi, L. Kandra, A. Liptak, Carbohydr. Res., 303 (1997) 407-415]. Shorter chain length CNP-maltooligosaccharides in the range of dp 3-6 were prepared using rabbit skeletal muscle glycogen phosphorylase b (EC 2.4.1.1). Detailed enzymological investigations revealed that the conversion of G7-CNP was highly dependent on the conditions of phosphorolysis. A 100% conversion of G7-CNP was achieved during 10 min in 1 M phosphate buffer (pH 6.8) at 30°C with the tetramer glycoside (77%) as the main product. Phosphorolysis at 10°C for 10 min resulted in 89% conversion and G4-, G5-, and G6-CNP oligomers were detected in the ratio of 29:26:34%, respectively. The reaction pattern was investigated using an HPLC system. The preparative scale isolation of G(3→6)-CNP glycosides was achieved by size-exclusion column chromatography (SEC) on Toyopearl HW-40 matrix. The productivity of the synthesis was improved by yields of up to 70-75%. Copyright (C) 1999 Elsevier Science Ltd.
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