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 journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1581-1585
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume62
Issue number8
DOIs
Publication statusPublished - 1998 Jan 1

Keywords

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

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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