Conversion of α-methyltropate to optically active α-phenylpropionate by tropate-degrading Rhodococcus sp. KU1314

Kenji Miyamoto, Shinji Hirokawa, Hiromichi Ohta

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Microorganisms which can assimilate tropate were screened from soil. Among them, we found a microorganism which has an ability to convert α-methyltropate to optically active α-phenylpropionate, and it was identified as Rhodococcus sp. KU1314. Substrate specificity of the microorganism has been studied. When the aryl group was phenyl, 4-methoxyphenyl and 2-naphthyl, the substrate gave optically active α-propionate in good yields. To estimate the reaction mechanism, some compounds considered to be the intermediates were subjected to the reaction. Both enantiomers of α-methyltropate were converted to (R)-α-phenylpropionate with almost the same enantiomeric excess (68 and 72% from R-and S-enantiomers, respectively) and yield (605 and 48% from R-and S-enantiomers, respectively).

Original languageEnglish
Pages (from-to)14-19
Number of pages6
JournalJournal of Molecular Catalysis B: Enzymatic
Volume46
Issue number1-4
DOIs
Publication statusPublished - 2007 May 2

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Phenylpropionates
Rhodococcus
Enantiomers
Microorganisms
Propionates
Substrate Specificity
Soil
Substrates
Soils

Keywords

  • α-Phenylpropionate
  • Enzymatic oxidation
  • Rhodococcus
  • Screening
  • Tropate

ASJC Scopus subject areas

  • Biochemistry
  • Catalysis
  • Process Chemistry and Technology

Cite this

Conversion of α-methyltropate to optically active α-phenylpropionate by tropate-degrading Rhodococcus sp. KU1314. / Miyamoto, Kenji; Hirokawa, Shinji; Ohta, Hiromichi.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 46, No. 1-4, 02.05.2007, p. 14-19.

Research output: Contribution to journalArticle

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AB - Microorganisms which can assimilate tropate were screened from soil. Among them, we found a microorganism which has an ability to convert α-methyltropate to optically active α-phenylpropionate, and it was identified as Rhodococcus sp. KU1314. Substrate specificity of the microorganism has been studied. When the aryl group was phenyl, 4-methoxyphenyl and 2-naphthyl, the substrate gave optically active α-propionate in good yields. To estimate the reaction mechanism, some compounds considered to be the intermediates were subjected to the reaction. Both enantiomers of α-methyltropate were converted to (R)-α-phenylpropionate with almost the same enantiomeric excess (68 and 72% from R-and S-enantiomers, respectively) and yield (605 and 48% from R-and S-enantiomers, respectively).

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