N -acetyltaurine
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| Surname | N -acetyltaurine | |||||||||
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2-acetamidoethanesulfonic acid ( IUPAC ) |
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| Molecular formula | C 4 H 9 NO 4 S | |||||||||
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| Molar mass | 167.18 g mol −1 | |||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
N- acetyltaurine or NAcT is an endogenous metabolic product . The biochemical formation of N -acetyltaurine is mainly based on the acetylation of taurine by acetate . An increase in the endogenous N -acetyltaurine concentration was observed after the consumption of alcohol and after increased physical activity ( ketoacidosis ).
history
N- acetyltaurine was first mentioned in 1990 as a component of cobwebs . Due to its high hygroscopicity , N- acetyltaurine contributes significantly to the flexibility of cobwebs.
N- acetyltaurine was first mentioned as a metabolic product of alcohol in 2012 on the basis of a study with mice. Another study, which dealt with the connection between endurance training and the associated increase in N -acetyltaurine concentration, followed in 2015. One year later, the first publication appeared, which dealt with N -acetyltaurine as an alcohol marker in a forensic context. The increase in the N- acetyltaurine concentration in human urine was investigated on the basis of a drinking study. An evaluation of N -acetyltaurine in human blood followed in 2017 .
Importance as alcohol consumption marker
N -acetyltaurine is a direct alcohol marker that arises from the oxidative breakdown of alcohol. Previously known alcohol markers such as fatty acid ethyl esters , ethyl glucuronide , ethyl sulfate and phosphatidylethanolamine reflect mainly the non-oxidative breakdown of alcohol by conjugation (biotransformation ).
The fact that N- acetyltaurine is an endogenous metabolic product reduces the informative value of the alcohol marker: it is necessary to differentiate between endogenous concentrations and alcohol-induced concentrations.
In a drinking study with a target blood alcohol concentration of 0.8 ‰, a ten-fold increase in the endogenous value was found in urine and only doubled in blood. The large differences between the N -acetyltaurine concentrations in blood and urine suggest a very efficient excretion of N -acetyltaurine via the kidneys.
analysis
N- acetyltaurine can be quantified using a combination of high performance liquid chromatography and mass spectrometry (MS / MS). Due to the high hydrophilicity of N -acetyltaurine, hydrophilic interaction chromatography (HILIC) is suitable for separating the analyte from matrix components.
literature
- Marc Luginbühl, Sofie Rutjens, Stefan König, Julien Furrer, Wolfgang Weinmann: N-Acetyltaurine as a novel urinary ethanol marker in a drinking study. In: Analytical and Bioanalytical Chemistry. 408, 2016, pp. 7529-7536, doi : 10.1007 / s00216-016-9855-7 .
- Torsten Arndt: N-acetyltaurine. In: Lexikon der Medizinischen Laboratoriumsdiagnostik , 3rd edition, planned for 2018. doi : 10.1007 / 978-3-642-12921-6 .
Individual evidence
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ a b Xiaolei Shi, Dan Yao, Chi Chen: Identification of N-Acetyltaurine as a Novel Metabolite of Ethanol through Metabolomics-guided Biochemical Analysis . In: Journal of Biological Chemistry . tape 287 , no. 9 , February 24, 2012, p. 6336-6349 , doi : 10.1074 / jbc.m111.312199 , PMID 22228769 .
- ↑ a b Teruo Miyazaki, Yuho Nakamura, Kei Ebina, Takaki Mizushima, Song-Gyu Ra: Increased N-Acetyltaurine in the Skeletal Muscle After Endurance Exercise in Rat . In: Taurine 10 (= Advances in Experimental Medicine and Biology ). Springer, Dordrecht, 2017, ISBN 978-94-024-1077-8 , pp. 403-411 , doi : 10.1007 / 978-94-024-1079-2_33 .
- ↑ a b c d Marc Luginbühl, Stefan König, Stefan Schürch, Wolfgang Weinmann: Evaluation of N-acetyltaurine as an ethanol marker in human blood . In: Alcohol . tape 65 , p. 11-18 , doi : 10.1016 / j.alcohol.2017.05.007 .
- ↑ a b c d Marc Luginbühl, Sofie Rutjens, Stefan König, Julien Furrer, Wolfgang Weinmann: N-Acetyltaurine as a novel urinary ethanol marker in a drinking study . In: Analytical and Bioanalytical Chemistry . tape 408 , no. 26 , October 1, 2016, p. 7529-7536 , doi : 10.1007 / s00216-016-9855-7 .
- ^ Fritz Vollrath, Wayne J. Fairbrother, Robert JP Williams, Edward K. Tillinghast, David T. Bernstein: Compounds in the droplets of the orb spider's viscid spiral . In: Nature . tape 345 , no. 6275 , June 7, 1990, pp. 526-528 , doi : 10.1038 / 345526a0 .