Enzymatic synthesis of 2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene beta-maltopentaoside, a substrate for alpha-amylase.
A transglycosylation reaction with 2-chloro-4-nitrophenyl beta-maltoside as an acceptor was done with 4,6-O-3-ketobutylidene maltopentaose and Bacillus macerans cyclodextrin glucanotransferase in an aqueous solution containing 50% n-propanol, and there were two main transglycosylation products. They were identified as 2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene beta-maltopentaoside and 2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene beta-maltohexaoside, and their yields were 30% and 21% respectively on the basis of the decrease of 4,6-O-3-ketobutylidene maltopentaose. For the production of 2-chloro-4-nitrophenyl 4,6-O-3-ketobutylidene beta-maltopentaoside at high substrates concentrations, the addition of n-propanol in this reaction not only increased the solubility of 2-chloro-4-nitrophenyl beta-maltoside sufficiently but also suppressed side reactions.
Chemical Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd., Fukuoka, Japan.
K
K
Ishimaru
Y
Y
Kamezono
S
S
Teshima
Y
Y
Hayashi
D000433:1-Propanol / Q000737:chemistry; D001407:Bacillus / Q000201:enzymology; D002240:Carbohydrate Sequence; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D005964:Glucosyltransferases / Q000378:metabolism; D006031:Glycosylation; D008969:Molecular Sequence Data; D009578:Nitrobenzenes / Q000737:chemistry; D000516:alpha-Amylases / Q000097:blood*
D005960:Glucosides; D009578:Nitrobenzenes; C071715:3-ketobutylidene 2-chloro-4-nitrophenylmaltopentaoside; C078908:2-chloro-4-nitrophenylmaltoside; C078907:4,6-O-3-ketobutylidene maltopentaose; D000433:1-Propanol; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase; D000516:alpha-Amylases