Identification of 1,4-thiomorpholine-3-carboxylic acid (TMA) in normal human urine

The sulfur-containing cyclic imino acid 1,4-thiomorpholine-3-carboxylic acid (TMA) has been identified in normal human urine. After the enrichment procedure with ion-exchange chromatography, the urine extracts were reacted with diazomethane. Gas-liquid chromatography revealed the presence of two peaks with the same retention times exhibited by authentic TMA after the same derivatization. The two compounds have been identified by mass-spectrometry as the monomethylated and dimethylated derivatives of TMA. This result represents the first indication of the occurrence of TMA in a mammalian sample.