Synthesis and evaluation of dihydro-[1,2,4]triazolo[4,3-a]pyridin-2-ium carboxylates as fixed charge fluorescent derivatization reagents for MEKC and MS proteomic analyses
Type
ArticleAuthors
Fedorowicz, JoannaCebrat, Marek
Wierzbicka, Magdalena
Wiśniewska, Paulina
Jalińska, Aleksandra
Dziomba, Szymon
Gdaniec, Maria
Jaremko, Mariusz

Jaremko, Lukasz

Chandra, Kousik
Szewczuk, Zbigniew
Sączewski, Jarosław
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionBioscience Program
Date
2020-05-14Online Publication Date
2020-05-14Print Publication Date
2020-10Submitted Date
2020-03-01Permanent link to this record
http://hdl.handle.net/10754/662834
Metadata
Show full item recordAbstract
Proteinogenic amino acids were derivatized via coupling reactions with N-hydroxysuccinimide esters of Safirinium dyes. The obtained compounds were fully characterized by 1H and 13C NMR, IR, and ESI-MS spectral techniques. Elemental analysis, as well as the crystal structure analysis of exemplary compounds, were performed. The absorption and fluorescent properties of the obtained derivatives have been systematically investigated. The optical properties and very good water solubility allowed for the development of a simple method for the determination of exemplary amino acids by means of micellar electrokinetic chromatography. Moreover, a new class of fluorescent peptide building blocks comprising a spiro-conjugated Safirinium-proline system was obtained. Due to the presence of a permanent positive charge, Safirinium-amino acid dervatives are potential candidates for signal enhancers in MS proteomic analysis. The applicability of the examined ionization tags in signal enhancement and peptide sequencing was proved. The obtained results provide an experimental basis for the development of a new approach for trace amino acids, peptides, and proteins detection by means of absorption, fluorescence, and mass spectrometry.Citation
Fedorowicz, J., Cebrat, M., Wierzbicka, M., Wiśniewska, P., Jalińska, A., Dziomba, S., … Sączewski, J. (2020). Synthesis and evaluation of dihydro-[1,2,4]triazolo[4,3-a]pyridin-2-ium carboxylates as fixed charge fluorescent derivatization reagents for MEKC and MS proteomic analyses. Journal of Molecular Structure, 128426. doi:10.1016/j.molstruc.2020.128426Sponsors
This work was supported by the Polish Ministry of Science and Higher Education (research grant IP2012 055472), KNOW programme and Medical University of Gdańsk subsidies [research grant number 01-0302/08/509], as well as by Wrocław Centre of Biotechnology and programme The Leading National Research Centre (KNOW) for years 2014-2018.Publisher
Elsevier BVJournal
Journal of Molecular StructureAdditional Links
https://linkinghub.elsevier.com/retrieve/pii/S0022286020307511https://doi.org/10.1016/j.molstruc.2020.128426
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Is Supplemented By:- [Dataset]
. DOI: 10.5517/ccdc.csd.cc23zt0y HANDLE: 10754/664889
- [Dataset]
. DOI: 10.5517/ccdc.csd.cc23zszw HANDLE: 10754/664890
ae974a485f413a2113503eed53cd6c53
10.1016/j.molstruc.2020.128426