A new type of N-nitrosamino acid, N-nitroso-L-thioproline and N-nitroso-L-methylthioprolines, found in human urine as major N-nitroso compounds. 1984

M Tsuda, and T Hirayama, and T Sugimura, and T Kakizoe

In addition to N-nitrosoproline (NPRO), N-nitrosamino acids of a new type containing sulfur were found as major N-nitroso compounds in the urine of seven healthy subjects. These compounds were detected using a gas chromatograph connected with a Thermal Energy Analyzer (GC-TEA), and they were identified as N-nitroso-L-thiazolidine-4-carboxylic acid (N-nitroso-L-thioproline, NTPRO) and the cis and trans isomers of N-nitroso-L-methylthiazolidine-4-carboylic acid (N-nitroso-L-methylthioproline, NMTPRO) by using gas chromatography-mass spectrometry (GC-MS). The amounts of NPRO, NTPRO and NMTPRO found in 100 mL samples of human urine were 65-471 ng, 67-2 250 ng and 275-5 825 ng, respectively. L-Thioproline was nitrosated 20-60 times faster than L-proline by nitrite over the whole range of acidic pH. The precursors of these new-N-nitrosamino acids containing sulfur may be formed by the reaction of L-cysteine with formaldehyde and acetaldehyde in the human body. These sulfur-containing N-nitroso compounds, NTPRO and NMTPRO, in addition to NPRO, could be useful as probes for investigation the dynamics of nitrosation in the human body.

UI MeSH Term Description Entries
D008401 Gas Chromatography-Mass Spectrometry A microanalytical technique combining mass spectrometry and gas chromatography for the qualitative as well as quantitative determinations of compounds. Chromatography, Gas-Liquid-Mass Spectrometry,Chromatography, Gas-Mass Spectrometry,GCMS,Spectrometry, Mass-Gas Chromatography,Spectrum Analysis, Mass-Gas Chromatography,Gas-Liquid Chromatography-Mass Spectrometry,Mass Spectrometry-Gas Chromatography,Chromatography, Gas Liquid Mass Spectrometry,Chromatography, Gas Mass Spectrometry,Chromatography, Mass Spectrometry-Gas,Chromatography-Mass Spectrometry, Gas,Chromatography-Mass Spectrometry, Gas-Liquid,Gas Chromatography Mass Spectrometry,Gas Liquid Chromatography Mass Spectrometry,Mass Spectrometry Gas Chromatography,Spectrometries, Mass-Gas Chromatography,Spectrometry, Gas Chromatography-Mass,Spectrometry, Gas-Liquid Chromatography-Mass,Spectrometry, Mass Gas Chromatography,Spectrometry-Gas Chromatography, Mass,Spectrum Analysis, Mass Gas Chromatography
D009602 Nitrosamines A class of compounds that contain a -NH2 and a -NO radical. Many members of this group have carcinogenic and mutagenic properties. Nitrosamine
D009603 Nitroso Compounds Organic compounds containing the nitroso (-N Compounds, Nitroso
D002849 Chromatography, Gas Fractionation of a vaporized sample as a consequence of partition between a mobile gaseous phase and a stationary phase held in a column. Two types are gas-solid chromatography, where the fixed phase is a solid, and gas-liquid, in which the stationary phase is a nonvolatile liquid supported on an inert solid matrix. Chromatography, Gas-Liquid,Gas Chromatography,Chromatographies, Gas,Chromatographies, Gas-Liquid,Chromatography, Gas Liquid,Gas Chromatographies,Gas-Liquid Chromatographies,Gas-Liquid Chromatography
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013844 Thiazoles Heterocyclic compounds where the ring system is composed of three CARBON atoms, a SULFUR and NITROGEN atoms. Thiazole
D053778 Thiazolidines Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES. Thiazolidine

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