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Substrate specificity of human monoamine (M)-form phenol sulfotransferase: preparation and analysis of Dopa 3-O-sulfate and Dopa 4-O-sulfate.

Abstract
Upon two-dimensional thin-layer separation, the sulfated L-3, 4-dihydroxyphenylalanine (L-DopaS) generated enzymatically was found to co-migrate with only one of the two ninhydrin-stained spots corresponding to the two sulfated forms (3-O-sulfate and 4-O-sulfate) of synthetic L-DopaS. To clarify precisely the identity of the enzymatically generated L-DopaS, the two sulfated forms of synthetic L-DopaS were separated and purified using high performance liquid chromatography. Purified L-Dopa 3-O-sulfate and L-Dopa 4-O-sulfate were identified by 1H-nuclear magnetic resonance (NMR) spectrometry and used as standards in the analysis of the L-DopaS generated during metabolic labeling of HepG2 human hepatoma cells or enzymatic assay using recombinant human monoamine (M)-form phenol sulfotransferase. The results obtained demonstrated unequivocally the generation of L-Dopa 3-O-sulfate, indicating the specificity of the M-form phenol sulfotransferase being for the meta-hydroxyl group of L-Dopa.
AuthorsM Suiko, Y Sakakibara, R Awan-Khan, H Sakaida, H Yoshikawa, J G Ranasinghe, M C Liu
JournalJournal of biochemistry (J Biochem) Vol. 124 Issue 4 Pg. 707-11 (Oct 1998) ISSN: 0021-924X [Print] England
PMID9756614 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • 3,4-dihydroxyphenylalanine 3-O-sulfate
  • 3,4-dihydroxyphenylalanine 4-O-sulfate
  • Isoenzymes
  • Sulfates
  • Sulfur Radioisotopes
  • Sulfuric Acid Esters
  • Levodopa
  • Arylsulfotransferase
Topics
  • Arylsulfotransferase (metabolism)
  • Carcinoma, Hepatocellular
  • Chromatography, Thin Layer
  • Humans
  • Isoenzymes (metabolism)
  • Levodopa (analogs & derivatives, chemistry, metabolism)
  • Liver Neoplasms
  • Magnetic Resonance Spectroscopy
  • Substrate Specificity
  • Sulfates (metabolism)
  • Sulfur Radioisotopes
  • Sulfuric Acid Esters (chemistry, metabolism)
  • Tumor Cells, Cultured

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