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Arginine-mimic labeling with guanidinoethanethiol to increase mass sensitivity of lysine-terminated phosphopeptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
Rapid Commun Mass Spectrom. 2007; 21(14):2204-10.RC

Abstract

Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) generally shows better mass sensitivity for arginine-terminated peptides than for lysine-terminated peptides, presumed to arise from the higher proton affinity of the guanidine group in arginine. Here, we report a new method for analyzing phosphopeptides in which phosphopeptides are labeled with a novel chemical tag, guanidinoethanethiol (GET), by a beta-elimination/Michael addition before MS analysis. GET labeling converts phosphoserine into guanidinoethylcysteine (Gec) containing a guanidine moiety, along with an increase in mass of 21.1 Da. GET-labeled peptides are detected by MALDI MS with greatly increased peak intensities compared to those of intact phosphopeptides. In particular, GET labeling of lysine-terminated phosphopeptides dramatically increased peak intensity. GET labeling of lysine-terminated phosphopeptides improved sensitivity up to 22 times compared to that of the corresponding aminoethanethiol (AET) labeling, in which AET was used as a labeling tag containing an amino group instead of the guanidine group. These results show the guanidine group plays a very important role in increasing the observed sensitivity of MALDI MS for labeled peptide, derivatized from serine-phosphorylated peptides.

Authors+Show Affiliations

Division of Instrument Development, Korea Basic Science Institute, Daejon 305-333, Korea.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17569100

Citation

Ahn, Yeong Hee, et al. "Arginine-mimic Labeling With Guanidinoethanethiol to Increase Mass Sensitivity of Lysine-terminated Phosphopeptides By Matrix-assisted Laser Desorption/ionization Time-of-flight Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 21, no. 14, 2007, pp. 2204-10.
Ahn YH, Ji ES, Lee JY, et al. Arginine-mimic labeling with guanidinoethanethiol to increase mass sensitivity of lysine-terminated phosphopeptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(14):2204-10.
Ahn, Y. H., Ji, E. S., Lee, J. Y., Cho, K., & Yoo, J. S. (2007). Arginine-mimic labeling with guanidinoethanethiol to increase mass sensitivity of lysine-terminated phosphopeptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 21(14), 2204-10.
Ahn YH, et al. Arginine-mimic Labeling With Guanidinoethanethiol to Increase Mass Sensitivity of Lysine-terminated Phosphopeptides By Matrix-assisted Laser Desorption/ionization Time-of-flight Mass Spectrometry. Rapid Commun Mass Spectrom. 2007;21(14):2204-10. PubMed PMID: 17569100.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Arginine-mimic labeling with guanidinoethanethiol to increase mass sensitivity of lysine-terminated phosphopeptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. AU - Ahn,Yeong Hee, AU - Ji,Eun Sun, AU - Lee,Ji Yeon, AU - Cho,Kun, AU - Yoo,Jong Shin, PY - 2007/6/15/pubmed PY - 2007/8/24/medline PY - 2007/6/15/entrez SP - 2204 EP - 10 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 21 IS - 14 N2 - Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) generally shows better mass sensitivity for arginine-terminated peptides than for lysine-terminated peptides, presumed to arise from the higher proton affinity of the guanidine group in arginine. Here, we report a new method for analyzing phosphopeptides in which phosphopeptides are labeled with a novel chemical tag, guanidinoethanethiol (GET), by a beta-elimination/Michael addition before MS analysis. GET labeling converts phosphoserine into guanidinoethylcysteine (Gec) containing a guanidine moiety, along with an increase in mass of 21.1 Da. GET-labeled peptides are detected by MALDI MS with greatly increased peak intensities compared to those of intact phosphopeptides. In particular, GET labeling of lysine-terminated phosphopeptides dramatically increased peak intensity. GET labeling of lysine-terminated phosphopeptides improved sensitivity up to 22 times compared to that of the corresponding aminoethanethiol (AET) labeling, in which AET was used as a labeling tag containing an amino group instead of the guanidine group. These results show the guanidine group plays a very important role in increasing the observed sensitivity of MALDI MS for labeled peptide, derivatized from serine-phosphorylated peptides. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/17569100/Arginine_mimic_labeling_with_guanidinoethanethiol_to_increase_mass_sensitivity_of_lysine_terminated_phosphopeptides_by_matrix_assisted_laser_desorption/ionization_time_of_flight_mass_spectrometry_ DB - PRIME DP - Unbound Medicine ER -