Synthesis and purification of racemic 2-(1-hydroxyethyl)thiamine revisited

James T. Stivers, Michael W. Washabaugh

Research output: Contribution to journalArticlepeer-review

Abstract

A procedure is reported for the rapid (≤1 day) and reproducible purification of 2-(1-hydroxyethyl)thiamine (HET) from contaminating thiamine (≤50%) using aqueous cation exchange chromatography. The unhydrated product contains ≤0.2% thiamine on the basis of its 1H NMR spectrum, visualization on silica gel TLC by fluorescence quenching after development in 60% aqueous ethanol, and the failure to observe the hydrolysis of thiamine using an iodine trapping assay under conditions where hydrolysis of ≤0.2% contaminating thiamine would have been detected. This purification procedure is also applicable to the resolved R and S stereoisomers of HET. Several literature procedures for the synthesis and purification of racemic HET are discussed and critically evaluated.

Original languageEnglish (US)
Pages (from-to)425-434
Number of pages10
JournalBioorganic Chemistry
Volume18
Issue number4
DOIs
StatePublished - Dec 1990

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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