Novel Enzymatic Synthesis of β-D-Galactosyl- and 6-O-Benzyl-Derivatives of p-Nitrophenyl α-Maltopentaoside

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  • p-ニトロフェニルβ-D-ガラクトシルおよび6-Oベンジル-α-マルトペンタオシドの新規酵素合成法
  • Novel Enzymatic Synthesis of ベータ D Gala

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The hydrolysis of various β-1, 4-galactosyl-maltooligosaccharides (β-1, 4-Gal-Gn) by the action of an exo-maltotetraohydrolase (EC 3.2.1.60, G4-amylase) from Pseudomonas stutzeri was examined to obtain information on action mode and kinetic parameters. The enzyme split 2 points of the. α-1, 4-glucosidic linkage in β-1, 4-galactosyl-maltotetraose (β-1, 4-Gal-G4) and 3 points in β-1, 4-Gal-G5, -Gal-G6 and -Gal-G7 to form various molar ratios of β-1, 4-Gal-G2, -Gal-G3 and -Gal-G4, respectively, and larger ko/Km values were observed with larger β-1, 4-Gal-Gn as substrates. The G4-amylase catalyzed the formation of p-nitrophenyl β-1, 4-D-galactosyl-α-maltopentaoside (β-1, 4-Gal-G5P) by its transfer action with a yield of 3.3, 11.3 and 6.8% by weight, and coincided well with the hydrolytic pattern of β-1, 4-Gal-Gn (n=5-7), from the mixture of p-nitrophenyl α-D-glucopyranoside (GP) and β-1, 4-Gal-G5, -Gal-G6 or -Gal-G7, respectively. The G4-amylase synthesized β-1, 4-Gal-G5P with a yield of 6.1% by weight of the mixture of GP with crude Gal-Gn containing primarily Gal-G6 and Gal-G7, of which about 10% was the respective β-1, 6 isomer. By an analogous method, the preparation of p-nitropheny16-0-benzyl-α-maltopentaoside (BG5P) was also examined with the mixture of GP and methyl 6-O-benzyl-α-maltooligosaccharides (BGn-Me) containing primarily BG6-Me and BG7-Me. In contrast to the action on Gal-Gn, the enzyme split 1 point of the α-1, 4-glucosidic linkage in BGn-Me, and the BG4 formed was readily transferred to the 4-position of GP by the α-1, 4-glucosidic linkage with a yield of 10.2% (w/w) . By these methods, the complicated procedures to obtain pure p-nitrophenyl α-malto-pentaoside (G5P) were eliminated from the conventional production methods of Gal-G5P and BG5P.

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