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

Atsuhito Kuboki, Ryosuke Komiya, Takahiro Sekiguchi, Kenji Katsuragi, Takeshi Sugai, Hiromichi Ohta

Research output: Contribution to journal › Article

4 Citations (Scopus)

Abstract

The substrate specificity was studied for the metabolic degradation of N-acetyl-D-glucosamine (GIcNAc) 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.

Original languageEnglish
Pages (from-to)1581-1585
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume62
Issue number8
Publication statusPublished - 1998 Aug

Fingerprint

Rhodococcus rhodochrous
Rhodococcus
Acetylglucosamine
glucosamine
substrate specificity
Substrate Specificity
chemical derivatives
Derivatives
Degradation
Microorganisms
synthesis
degradation
Substrates
microorganisms
Hexosaminidases
Aldehydes
aldehydes
Enzymes
enzymes

Keywords

  • β-N-acetyl-D-glucosaminidase
  • Allyl α-N-acetyl-D-glucosaminide
  • N-acetyl-D-glucosamine
  • N-acetyl-D-glucosamine deacetylase
  • Rhodococcus rhodochrous IFO 15564

ASJC Scopus subject areas

  • Food Science
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biotechnology
  • Chemistry (miscellaneous)
  • Applied Microbiology and Biotechnology

Cite this

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. / Kuboki, Atsuhito; Komiya, Ryosuke; Sekiguchi, Takahiro; Katsuragi, Kenji; Sugai, Takeshi; Ohta, Hiromichi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 62, No. 8, 08.1998, p. 1581-1585.

Research output: Contribution to journal › Article

Kuboki, A, Komiya, R, Sekiguchi, T, Katsuragi, K, Sugai, T & Ohta, H 1998, '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', Bioscience, Biotechnology and Biochemistry, vol. 62, no. 8, pp. 1581-1585.
Kuboki A, Komiya R, Sekiguchi T, Katsuragi K, Sugai T, Ohta H. 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. Bioscience, Biotechnology and Biochemistry. 1998 Aug;62(8):1581-1585.
Kuboki, Atsuhito ; Komiya, Ryosuke ; Sekiguchi, Takahiro ; Katsuragi, Kenji ; Sugai, Takeshi ; Ohta, Hiromichi. / 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. In: Bioscience, Biotechnology and Biochemistry. 1998 ; Vol. 62, No. 8. pp. 1581-1585.
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