Enzymatic Synthesis of Acarviosyl-maltooligosaccharides Using Disproportionating Enzyme 1

• Published in: Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2013, Vol.77 (2), p.312-319
• Main Authors: TAGAMI, Takayoshi, TANAKA, Yoshiyuki, MORI, Haruhide, OKUYAMA, Masayuki, KIMURA, Atsuo
• Format: Article
• Language: English
• Subjects: acarbose; Acarbose - chemistry; acarviosyl-maltooligosaccharide; Amino Acid Sequence; Biocatalysis; Carbohydrate Sequence; disproportionating enzyme 1; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Fabaceae - chemistry; Fabaceae - enzymology; Glycogen Debranching Enzyme System - chemistry; Glycogen Debranching Enzyme System - isolation & purification; glycoside hydrolase family 77; Glycoside Hydrolases - antagonists & inhibitors; inhibitor; Molecular Sequence Data; Oligosaccharides - chemical synthesis; Oligosaccharides - chemistry; Plant Proteins - chemistry; Plant Proteins - isolation & purification; Polymerization
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.120732

Acarbose is a pseudo-tetrasaccharide and one of the most effective inhibitors of glycoside hydrolases. Its derivatives, acarviosyl-maltooligosaccharides, which have longer maltooligosaccharide parts than the maltose unit of acarbose, were synthesized using a disproportionating enzyme partially purified from adzuki cotyledons. The enzyme was identified as a typical type-1 disproportionating enzyme (DPE1) by primary structure analysis. It produced six compounds from 100 mM acarbose and 7.5% (w/v) of maltotetraose-rich syrup. The masses of the six products were confirmed to accord with acarviosyl-maltooligosaccharides with the degrees of polymerization = 5-10 (AC5-AC10) by electrospray ionization mass spectrometry. (1)H and (13)C NMR spectra indicated that AC5-AC10 were α-acarviosyl-(1→4)-maltooligosaccharide, which have maltotriose-maltooctaose respectively in the maltooligosaccharide part. A predominance of AC7 in the products at the early stage of the reaction indicated that DPE1 catalyzes the transfer of the acarviosyl-glucose moiety from acarbose to the acceptors. ACn can be useful tools as new inhibitors of glycoside hydrolases.