Abstract
(5-N-Succinimidoxy-5-oxopentyl)triphenylphosphonium bromide (SPTPP) is a highly sensitive and positively charged precolumn derivatization reagent for the analysis of amino acids in liquid chromatography–electrospray ionization-tandem mass spectrometry. The synthesis of this reagent and handling of the derivatization reaction are quite simple. It reacts with amino acids rapidly and with high efficiency. MS/MS analysis revealed that the SPTPP-derivatized amino acids formed strong product ions; thus, highly sensitive and selective detection is possible in the selected reaction monitoring mode. The limits of detection for the SPTPP-derivatized amino acids are in the sub-fmol range. The sensitivities of the derivatized amino acids increased about 500-fold, as compared to those of underivatized amino acids.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Dixon RW and Peterson DS (2002) Development and testing of a detection method for liquid chromatography based on aerosol charging. Anal Chem 74: 2930–2937
Barry SJ et al (2003) Derivatisation for liquid chromatography/electrospray mass spectrometry: synthesis of pyridinium compounds and their amine and carboxylic acid derivatives. Rapid Commun Mass Spectrom 17:603–620
Zaikin VG and Halket JM (2006) Derivatization in mass spectrometry. 8. Soft ionization mass spectrometry of small molecules. Eur J Mass Spectrom 12:79–115
Santa T et al (2007) Derivatization reagents in liquid chromatography/electrospray ionization tandem mass spectrometry for biomedical analysis. Drug Discov Ther 1:108–118
Shimbo K et al (2009) Multifunctional and highly sensitive precolumn reagents for amino acids in liquid chromatography/tandem mass spectrometry. Anal Chem 81:5172–5179
Shimbo K et al (2009) Precolumn derivatization reagents for high-speed analysis of amines and amino acids in biological fluid using liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom 23:1483–1492
Shimbo K et al (2010) Automated precolumn derivatization system for analyzing physiological amino acids by liquid chromatography/mass spectrometry. Biomed Chromatogr 24:683–691
Inagaki S et al (2010) Highly sensitive and positively charged precolumn derivatization reagent for amines and amino acids in liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 24:1358–1364
Acknowledgments
The authors thank Mr. Yuma Tano and Mr. Yusuke Yamakata for their support with the experiments. This work was supported in part by an academic research grant from the Shimadzu Science Foundation and by the Global COE Program of the Ministry of Education, Culture, Sports, Science and Technology, Japan.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer Science+Business Media, LLC
About this protocol
Cite this protocol
Inagaki, S., Toyo’oka, T. (2012). Amino Acid Analysis via LC–MS Method After Derivatization with Quaternary Phosphonium. In: Alterman, M., Hunziker, P. (eds) Amino Acid Analysis. Methods in Molecular Biology, vol 828. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-61779-445-2_5
Download citation
DOI: https://doi.org/10.1007/978-1-61779-445-2_5
Published:
Publisher Name: Humana Press, Totowa, NJ
Print ISBN: 978-1-61779-444-5
Online ISBN: 978-1-61779-445-2
eBook Packages: Springer Protocols