Control of the nitrile-hydrolyzing enzyme activity in Rhodococcus rhodochrous IFO 15564

Preferential action of nitrile hydratase and amidase depending on the reaction condition factors and its application to the one-pot preparation of amides from aldehydes

Mieko Kashiwagi, Ken Ichi Fuhshuku, Takeshi Sugai

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The reaction conditions towards the preferential action of either nitrile hydratase or amidase in the harvested whole cells of Rhodococcus rhodochrous IFO 15564 were elaborated. The amidase showed higher heat tolerance than the nitrile hydratase and, at 45°C the amidase worked exclusively. DMSO assisted the preferential action of nitrile hydratase, however, at more than 30% (v/v) addition of DMF, the nitrile hydratase activity was completely lost and only amidase worked. A one-pot chemo-enzymatic conversion of aldehydes to amides [(1) aq. NH3, I2, DMSO; (2) Na2S2O 3; (3) harvested cells of R. rhodochrous] was established. Under these reaction conditions, most of the amidase was lost, and the incubation of the firstly formed intermediates, nitriles in aq. NH3 was responsible for the selective inhibition of amidase. The freezing of harvested cells in an exhaustively deionized environment provided a long-term preservable "ready to use" for the organic chemist.

Original languageEnglish
Pages (from-to)249-258
Number of pages10
JournalJournal of Molecular Catalysis B: Enzymatic
Volume29
Issue number1-6
DOIs
Publication statusPublished - 2004 Jun 21

Fingerprint

amidase
Rhodococcus
Nitriles
Enzyme activity
Aldehydes
Amides
Freezing
Enzymes
Dimethyl Sulfoxide
nitrile hydratase
Hot Temperature

Keywords

  • Amidase
  • Enzyme inhibition
  • Nitrile hydratase
  • One-pot synthesis of amides
  • Rhodococcus rhodochrous IFO 15564

ASJC Scopus subject areas

  • Biochemistry
  • Catalysis
  • Process Chemistry and Technology

Cite this

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title = "Control of the nitrile-hydrolyzing enzyme activity in Rhodococcus rhodochrous IFO 15564: Preferential action of nitrile hydratase and amidase depending on the reaction condition factors and its application to the one-pot preparation of amides from aldehydes",
abstract = "The reaction conditions towards the preferential action of either nitrile hydratase or amidase in the harvested whole cells of Rhodococcus rhodochrous IFO 15564 were elaborated. The amidase showed higher heat tolerance than the nitrile hydratase and, at 45°C the amidase worked exclusively. DMSO assisted the preferential action of nitrile hydratase, however, at more than 30{\%} (v/v) addition of DMF, the nitrile hydratase activity was completely lost and only amidase worked. A one-pot chemo-enzymatic conversion of aldehydes to amides [(1) aq. NH3, I2, DMSO; (2) Na2S2O 3; (3) harvested cells of R. rhodochrous] was established. Under these reaction conditions, most of the amidase was lost, and the incubation of the firstly formed intermediates, nitriles in aq. NH3 was responsible for the selective inhibition of amidase. The freezing of harvested cells in an exhaustively deionized environment provided a long-term preservable {"}ready to use{"} for the organic chemist.",
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