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The unexpected racemization and hydrogen–deuterium exchange of the hydrogen at the α-carbon of proline analogs containing the 5-azoniaspiro[4.4]nonyl-group

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Abstract

Recently, we developed a novel non-fragmenting quaternary ammonium ionization tag for the mass spectrometric sensitive sequencing of peptides, based on the N-spiro proline residue (5-azoniaspiro[4.4.]nonyl-carbonyl). Herein, we present an unexpected racemization and the hydrogen–deuterium exchange (HDX) at the α-C atom of the proline derivative under basic aqueous conditions (1% water solution of triethylamine). The deuterium atom, substituted for the α-C atom, does not undergo back-exchange under acidic aqueous conditions which makes the deuterated isotopologue a promising stabile isotope-coded internal standard for quantitative analysis by mass spectrometry. The applicability of the prepared isotopologues of the quaternary ammonium salt labeled peptides for quantification experiments using the isotopic dilution method was also examined.

Graphical abstract: The unexpected racemization and hydrogen–deuterium exchange of the hydrogen at the α-carbon of proline analogs containing the 5-azoniaspiro[4.4]nonyl-group

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Publication details

The article was received on 27 Nov 2017, accepted on 05 Jan 2018 and first published on 05 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02926H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    The unexpected racemization and hydrogen–deuterium exchange of the hydrogen at the α-carbon of proline analogs containing the 5-azoniaspiro[4.4]nonyl-group

    B. Setner, M. Wierzbicka, L. Jerzykiewicz, M. Lisowski and Z. Szewczuk, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02926H

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