Convenient preparation of deuterium‐labeled analogs of peptides containing N‐substituted glycines for a stable isotope dilution LC‐MS quantitative analysis. (29th September 2015)

• Record Type: Journal Article
• Authors: Bąchor, Remigiusz; Dębowski, Dawid; Łęgowska, Anna; Stefanowicz, Piotr; Rolka, Krzysztof; Szewczuk, Zbigniew
• Is Part Of: Journal of peptide science. Volume 21:Number 11(2015:Nov.)
• Page Start: 819
• Page End: 825
• Publication Date: 2015-09-29
• Subjects: Peptides -- Periodicals; Peptides -- Periodicals; 572.65
• DOI: 10.1002/psc.2823
• Languages: English
• ISSNs: 1075-2617

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <italic>N</italic>‐substituted glycines constitute mimics of natural amino acids that are of great interest in the peptide‐based drug development. Peptoids‐oligo(<italic>N</italic>‐substituted glycines) have been recently demonstrated to be highly active peptidomimetics in biological systems, resistant to proteolytic degradation.</p> <p>We developed a method of the deuterium labeling of peptidomimetics containing <italic>N</italic>‐substituted glycine residues via H/D exchange of their <italic>α</italic>‐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 <italic>α</italic>‐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 <italic>N</italic>‐substituted glycines. Copyright © 2015 European Peptide Society and John Wiley &amp; Sons, Ltd.</p> </abstract>