Premium
Synthesis of 3‐nitro‐L‐[ 2 H 3 ]tyrosine for use as an internal standard for quantification of 3‐nitro‐L‐tyrosine by gas chromatography‐mass spectrometry
Author(s) -
Schwedhelm Edzard,
Sandmann Jörg,
Tsikas Dimitrios
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(1998080)41:8<773::aid-jlcr126>3.0.co;2-c
Subject(s) - chemistry , nitro , tyrosine , mass spectrometry , gas chromatography , chromatography , gas chromatography–mass spectrometry , organic chemistry , biochemistry , alkyl
3‐Nitro‐L‐tyrosine is produced in vitro and in vivo by the nitration of tyrosine and tyrosine residues in proteins. Plasma 3‐nitro‐L‐tyrosine has been suggested as an index of oxidative damage in living organisms that depend on nitrating species. For use in the quantitative determination of 3‐nitro‐L‐tyrosine in biological fluids by gas chromatography‐mass spectrometry (GC‐MS) we describe the chemical synthesis of 3‐nitro‐L‐[ 2 H 3 ] tyrosine by nitration of commercially available L‐[ 2 H 4 ] tyrosine by nitrate and sulphuric acid. GC‐MS analysis revealed a 2 H isotopic purity of about 98%. The isolated reaction product did not contain any detectable amounts of L‐[ 2 H 4 ] tyrosine. The utility of 3‐nitro‐L‐[ 2 H 3 ]tyrosine as an internal standard for the quantitative analysis of 3‐nitro‐L‐tyrosine by GC‐MS is shown. © 1998 John Wiley & Sons, Ltd.