title: Synthesis of a chitosan tetramer derivative, beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-D-Glc N through a partial N-acetylation reaction by chitin deacetylase.
abstract: We have synthesized beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-D-GlcN (2) through a partial N-acetylation reaction of chitosan tetramer 1 by a chitin deacetylase from Colletotrichum lindemuthianum ATCC 56676. The compound was purified from the mixture of acetylation products of 1 using cation-exchange column chromatography and amine-adsorption column chromatography, and its structure was estimated by 1H NMR and FABMS analyses. The enzymatic reaction allows a regioselectivity that is hard to achieve by chemical N-acetylation.
authors.affiliation: National Food Research Institute, Tsukuba, Ibaraki, Japan. tokuyasu@nfri.affrc.go.jp
authors.forename: K
authors.initials: K
authors.lastname: Tokuyasu
authors.forename: H
authors.initials: H
authors.lastname: Ono
authors.forename: M
authors.initials: M
authors.lastname: Mitsutomi
authors.forename: K
authors.initials: K
authors.lastname: Hayashi
authors.forename: Y
authors.initials: Y
authors.lastname: Mori
mesh_terms: D000107:Acetylation; D000581:Amidohydrolases / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002686:Chitin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D048271:Chitosan; D020231:Colletotrichum / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D013997:Time Factors
chemical_list: C410296:GlcNAc-(1-4)-GlcNAc-(1-4)-GlcNAc-(1-4)-GlcN; D002686:Chitin; D048271:Chitosan; D000581:Amidohydrolases; C019866:chitin deacetylase