title: An enzymatically produced novel cyclic tetrasaccharide, cyclo-{-->6)-alpha-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->6)-alpha-D-Glcp-(1-->4)-alpha-D-Glcp-(1-->} (cyclic maltosyl-(1-->6)-maltose), from starch.
abstract: A bacterial strain M6, isolated from soil and identified as Arthrobacter globiformis, produced a novel nonreducing oligosaccharide. The nonreducing oligosaccharide was produced from starch using a culture supernatant of the strain as enzyme preparation. The oligosaccharide was purified as a crystal preparation after alkaline treatment and deionization of the reaction mixture. The structure of the oligosaccharide was determined by methylation analysis, mass spectrometry, and (1)H and (13)C NMR spectroscopy, and it was demonstrated that the oligosaccharide had a cyclic structure consisting of four glucose residues joined by alternate alpha-(1-->4)- and alpha-(1-->6)-linkages. The cyclic tetrasaccharide, cyclo-{-->6)-alpha-D-Glcp(1-->4)-alpha-D-Glcp(1-->6)-alpha-D-Glcp(1-->4)-alpha-D-Glcp(1-->}, was found to be a novel oligosaccharide, and was tentatively called cyclic maltosyl-maltose (CMM). CMM was not hydrolyzed by various amylases, such as alpha-amylase, beta-amylase, glucoamylase, isoamylase, pullulanase, maltogenic alpha-amylase, and alpha-glucosidase, but hydrolyzed by isomalto-dextranase to give rise to isomaltose. This is the first report of the cyclic tetrasaccharide, which has alternate alpha-(1-->4)- and alpha-(1-->6)-glucosidic linkages.
authors.affiliation: Amase Institute, Hayashibara Biochemical Laboratories, Inc., Okayama, Japan. k-mukai@hayashibara.co.jp
authors.forename: Kazuhisa
authors.initials: K
authors.lastname: Mukai
authors.forename: Hikaru
authors.initials: H
authors.lastname: Watanabe
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Oku
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Nishimoto
authors.forename: Michio
authors.initials: M
authors.lastname: Kubota
authors.forename: Hiroto
authors.initials: H
authors.lastname: Chaen
authors.forename: Shigeharu
authors.initials: S
authors.lastname: Fukuda
authors.forename: Masashi
authors.initials: M
authors.lastname: Kurimoto
mesh_terms: D001173:Arthrobacter / Q000201:enzymology*; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003500:Cyclization; D047028:Macrocyclic Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000737:chemistry; D008745:Methylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D012995:Solubility; D013213:Starch / Q000737:chemistry / Q000378:metabolism*; D013696:Temperature
chemical_list: D047028:Macrocyclic Compounds; D009844:Oligosaccharides; C504607:cyclo(-6)-glucopyranosyl-1-4-glucopyranosyl-1-6-glucopyranosyl-1-4-glucopyranosyl-(1-); D008320:Maltose; D013213:Starch