Hexahydro-1,4-thiazepine-3,5-dicarboxylic Acid and Thiomorpholine-3,5-dicarboxylic Acid are Present in Normal Human Urine

Hexahydro-1,4-thiazepine-3,5-dicarboxylic acid and thiomorpholine-3,5-dicarboxylic acid, simply referred to as cyclothionine and TMDA, respectively, are two cyclic sulfur-containing imino acids detected in bovine brain. Human urine has been investigated to establish the occurrence of these imino aci...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 1987-08, Vol.84 (15), p.5111-5114
Main Authors: Matarese, R. M., Pecci, L., Ricci, G., Nardini, M., Antonucci, A., Cavallini, D.
Format: Article
Language:English
Subjects:
Adult
Biochemistry
Chromatography
Chromatography, Gas
Chromatography, High Pressure Liquid
Evaporators
Female
Gas Chromatography-Mass Spectrometry
Humans
Imino acids
Imino Acids - urine
Ions
Male
Molecular ions
Morpholines - urine
Solvents
Thiazepines - urine
Ungulates
Urine
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Summary:Hexahydro-1,4-thiazepine-3,5-dicarboxylic acid and thiomorpholine-3,5-dicarboxylic acid, simply referred to as cyclothionine and TMDA, respectively, are two cyclic sulfur-containing imino acids detected in bovine brain. Human urine has been investigated to establish the occurrence of these imino acids as common constituents under normal conditions. The morning urine of healthy subjects has been analyzed for enrichment of these compounds by using an ion-exchange procedure. Gas/liquid chromatography of the final extracts revealed the presence of peaks coeluting with authentic cyclothionine and TMDA. The latter compound eluted very close to an unknown sulfur-containing compound. A resolved peak of TMDA has been obtained by high-performance liquid chromatography of the final extracts derivatized with phenylisothiocyanate. Selected ion monitoring with multiple-ion detection applied to the compounds separated by gas chromatography revealed the presence of the respective molecular ions and of the decarboxylated fragments, thus confirming the identification of cyclothionine and TMDA in human urine.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.84.15.5111