Carbolines mass spectrometry

Using the powerful structural elucidation technique of tandem mass spectrometry coupled with on-line HPLC (LC-ESI-MS/MS), the structural characterization of a number of additional contaminants of L-tryptophan associated with EMS has been performed.18 The identity of the contaminants were as follows. Peaks UV-5 included 3-phenylamino-L-alanine (PAA) l,l -ethylidenebis(tryptophan) (EBT) 2-(3-indolymethyl)-L-tryptophan (200) (all identified as case related). Peaks 1,3-carboxyl-1,2,3,4-tetrahydro-p-carboline 2,3-carboxy-l-methyl-l,2,3,4-tetrahydro-P-carboline 2-(2,3 dihy-droxy-l-[3-indolyl]-propyl)-L-tryptophan (100) and diastereomers of 3-car-boxy-l-[3-indolyl-methyl]-l,2,3,4 tetrahydro-P-carboline (300 and 400), were confirmed by this technique. Peak P31, previously unresolved from peak 200, a case-related compound, has been tentatively identified as 2-(3-indolyl)-L-tryptophan. Thus, progress on structural analyses of contaminants has progressed far beyond studies evaluating their toxicologic and physiologic potentials. 

Adachi, J., Mizoi, Y., Naito, T., Yamamoto, K., Fujiwara, S. and Ninomiya, 1. (1991b) Determination of beta-carbolines in foodstuffs by high-performance liquid chromatography-mass spectrometry. J. Chromatogr. 538 331-339. 

Back, Y. M., Lee, J. H., Shin, H. S., and Lxe, K. G. 2009. Analysis of heterocyclic amines and 3-carbolines by liquid chromatography-mass spectrometry in cooked meats commonly consumed in Korea. FoodAddit. Contam. 26 298-305. 

Gutsche B., Herderich M. High-performance liquid chromatography-electrospray ionisation-tandem mass spectrometry for the analysis of 1,2,3,4-tetrahydro-fi-carboline derivatives. Journal of Chromatography A, 767 101-106(1997). 

Nonami, H. Fukui, S. Erra-Balsells, R. P-Carboline alkaloids as matrices for matrix-assisted ultraviolet laser desorption time-of-flight mass spectrometry of proteins and sulfated oligosaccharides a comparative study using phenylcarbonyl compounds, carbazoles and classical matrices. J. Mass Spectrom. 1997, 32, 287 296. 

Nonami, H. Tanaka, K. Fukuyama, Y. Erra-Balsells, R. P-Carboline alkaloids as matrices IotUV-matrix-assisted laser desOTption/ionization time-of-flight mass spectrometry in positive and negative ion modes. Analysis of proteins of high molecular mass, and of cyclic and acyclic oligosaccharides. Rapid Commun. Mass Spectrum. 1998, 12, 285-296. 

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