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Convenient preparation of deuterium‐labeled analogs of peptides containing N ‐substituted glycines for a stable isotope dilution LC‐MS quantitative analysis
Author(s) -
Bąchor Remigiusz,
Dębowski Dawid,
Łęgowska Anna,
Stefanowicz Piotr,
Rolka Krzysztof,
Szewczuk Zbigniew
Publication year - 2015
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2823
Subject(s) - chemistry , derivatization , peptidomimetic , deuterium , isotope dilution , reagent , chromatography , isotopic labeling , peptide , mass spectrometry , isotopologue , elution , amino acid , combinatorial chemistry , organic chemistry , molecule , biochemistry , physics , quantum mechanics
N ‐substituted glycines constitute mimics of natural amino acids that are of great interest in the peptide‐based drug development. Peptoids‐oligo( N ‐substituted glycines) have been recently demonstrated to be highly active peptidomimetics in biological systems, resistant to proteolytic degradation. We developed a method of the deuterium labeling of peptidomimetics containing N ‐substituted glycine residues via H/D exchange of their α ‐carbon hydrogen atoms. The labeling was shown to be easy, inexpensive, and without the use of derivatization reagents or the need for a further purification. The deuterons introduced at the α ‐carbon atoms do not undergo a back exchange under acidic conditions during liquid chromatography mass spectrometry (LC‐MS) analysis. The LC‐MS analysis of a mixture of isotopologues revealed a co‐elution of deuterated and nondeuterated forms of the peptidomimetics, which may be useful in the quantitative isotope dilution analysis of peptoids and other derivatives of N ‐substituted glycines. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.