title: Degradation of Derivatives of N-Acetyl-D-glucosamine by Rhodococcus rhodochrous IFO 15564: Substrate Specificity and Its Application to the Synthesis of Allyl α-N-Acetyl-D-glucosaminide.
abstract: The substrate specificity was studied for the metabolic degradation of N-acetyl-D-glucosamine (GlcNAc) derivatives by Rhodococcus rhodochrous IFO 15564 which possesses N-acetyl-D-glucosamine deacetylase as a key-step enzyme. This microorganism degraded a wide range of substrates with modified N-acyl groups. The metabolizing activity of this strain became low to the substrates substituted at 1,3,4,6-positions of GlcNAc, and GlcNAc itself was suggested to be metabolized via an open-chain aldehyde form. Based on these results, a simplified procedure for the isolation of allyl α-N-acetyl-D-glucosaminide from an α, β-anomeric mixture was developed by selectively hydrolyzing the β-anomer with Jackbean β-N-acetyl-D-glucosaminidase and subsequently degrading the resulting N-acetyl-D-glucosamine in the reaction mixture with this microorganism.
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: A
authors.initials: A
authors.lastname: Kuboki
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: R
authors.initials: R
authors.lastname: Komiya
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: T
authors.initials: T
authors.lastname: Sekiguchi
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: K
authors.initials: K
authors.lastname: Katsuragi
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: T
authors.initials: T
authors.lastname: Sugai
authors.affiliation: a Department of Chemistry, Keio University.
authors.forename: H
authors.initials: H
authors.lastname: Ohta
keywords: N-acetyl-D-glucosamine; N-acetyl-D-glucosamine deacetylase; Rhodococcus rhodochrous IFO 15564; allyl α-N-acetyl-D-glucosaminide; β-N-acetyl-D-glucosaminidase