title: Enzymatic synthesis of Acarviosyl-maltooligosaccharides using disproportionating enzyme 1.
abstract: 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.
authors: Hokkaido University, Sapporo, Japan.
authors: Takayoshi
authors: T
authors: Tagami
authors: Yoshiyuki
authors: Y
authors: Tanaka
authors: Haruhide
authors: H
authors: Mori
authors: Masayuki
authors: M
authors: Okuyama
authors: Atsuo
authors: A
authors: Kimura
mesh_terms: D020909:Acarbose / Q000737:chemistry*; D000595:Amino Acid Sequence; D055162:Biocatalysis; D002240:Carbohydrate Sequence; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D007887:Fabaceae / Q000737:chemistry* / Q000201:enzymology; D006004:Glycogen Debranching Enzyme System / Q000737:chemistry* / Q000302:isolation & purification; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010940:Plant Proteins / Q000737:chemistry* / Q000302:isolation & purification; D058105:Polymerization
chemical_list: D004791:Enzyme Inhibitors; D006004:Glycogen Debranching Enzyme System; D009844:Oligosaccharides; D010940:Plant Proteins; C021705:maltooligosaccharides; C020569:4 alpha-glucanotransferase; D006026:Glycoside Hydrolases; D020909:Acarbose