Degradation of (+/-)-synephrine by Arthrobacter synephrinum. Oxidation of 3,4-dihydroxyphenylacetate to 2-hydroxy-5-carboxymethyl-muconate semialdehyde

Biochem J. 1977 Oct 1;167(1):163-70. doi: 10.1042/bj1670163.

Abstract

1. Cell-free extracts of Arthrobacter synephrinum catalyse the oxidation of 3,4-dihydroxy-phenylacetate. 2. The product of oxidation was characterized as 2-hydroxy-5-carboxymethylmuconate semialdehyde from its chemical behaviour as well as from nuclear-magnetic-resonance spectra. 3. A 3,4-dihydroxyphenylacetate 2,3-dioxygenase (EC 1.13.11.15) was partially purified from A. synephrinum. 4. The enzyme had a Km of 25 micrometer towards its substrate and exhibited typical Michaelis-Menten kinetics. 5. The enzyme also catalysed the oxidation of 3,4-dihydroxymandelate and 3,4-dihydroxyphenylpropionate, at reaction rates of 0.5 and 0.04 respectively of that for 3,4-dihydroxyphenylacetate. 6. The enzyme was sensitive to treatment with thiol-specific reagents. 7. The molecular weight of the enzyme as determined by Sephadex G-200 chromatography was approx. 282000.

MeSH terms

  • 3,4-Dihydroxyphenylacetic Acid / analogs & derivatives
  • 3,4-Dihydroxyphenylacetic Acid / metabolism*
  • Aldehydes
  • Arthrobacter / metabolism*
  • Dioxygenases
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Oxygenases / isolation & purification
  • Phenylacetates / metabolism*
  • Substrate Specificity
  • Sulfhydryl Compounds / pharmacology
  • Synephrine / metabolism*

Substances

  • Aldehydes
  • Phenylacetates
  • Sulfhydryl Compounds
  • 3,4-Dihydroxyphenylacetic Acid
  • 2-hydroxy-5-carboxymethylmuconate semialdehyde
  • Oxygenases
  • Dioxygenases
  • 3,4-dihydroxyphenylacetate 2,3-dioxygenase
  • Synephrine