title: Enzymatic synthesis of an α-chitin-like substance via lysozyme-mediated transglycosylation.
abstract: The enzymatic synthesis of an α-chitin-like substance via a non-biosynthetic pathway has been achieved by transglycosylation in an aqueous system of the corresponding substrate, tri-N-acetylchitotriose [(GlcNAc)(3)] for lysozyme. A significant amount of water-insoluble product precipitated out from the reaction system. MALDI-TOFMS analysis showed that the resulting precipitate had a degree of polymerization (DP) of up to 15 from (GlcNAc)(3). Solid-state (13)C NMR analysis revealed that the resulting water-insoluble product is a chitin-like substance consisting of N-acetylglucosamine (GlcNAc) residues joined exclusively in a β-(1→4)-linked chain with stringent regio-/stereoselection. X-ray diffraction (XRD) measurement as well as (13)C NMR analysis showed that the crystal structure of synthetic product corresponds to α-chitin with a high degree of crystallinity. We propose that the multiple oligomers form an α-chitin-like substance as a result of self-assembly via oligomer-oligomer interaction when they precipitate.
authors.affiliation: Department of Bioscience, Graduate School of Science and Technology, Shizuoka University, Ohya 836, Suruga Ward, Shizuoka 422-8529, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Hattori
authors.forename: Yoko
authors.initials: Y
authors.lastname: Sakabe
authors.forename: Makoto
authors.initials: M
authors.lastname: Ogata
authors.forename: Kousuke
authors.initials: K
authors.lastname: Michishita
authors.forename: Hideo
authors.initials: H
authors.lastname: Dohra
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Kawagishi
authors.forename: Kazuhide
authors.initials: K
authors.lastname: Totani
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Nikaido
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakamura
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
authors.forename: Taichi
authors.initials: T
authors.lastname: Usui
mesh_terms: D002240:Carbohydrate Sequence; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D002686:Chitin / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D055772:Green Chemistry Technology / Q000379:methods*; D008837:Micrococcus / Q000201:enzymology; D008969:Molecular Sequence Data; D009113:Muramidase / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D002686:Chitin; D009113:Muramidase