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Synthesis and mass spectrometry analysis of quaternary cryptando‐peptidic conjugates
Author(s) -
Bąchor Remigiusz,
Kluczyk Alicja,
Stefanowicz Piotr,
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.2830
Subject(s) - chemistry , cryptand , moiety , peptide , tandem mass spectrometry , mass spectrometry , conjugate , crown ether , combinatorial chemistry , solid phase synthesis , fragmentation (computing) , peptide synthesis , ether , stereochemistry , organic chemistry , chromatography , ion , mathematical analysis , biochemistry , mathematics , computer science , operating system
The bicyclic amines in the form of cryptands, the crown ether analogs, were used in the synthesis of cryptando‐peptidic conjugates with simultaneous formation of quaternary ammonium nitrogen moiety. A series of model cryptando‐peptidic conjugates at the peptide N ‐terminus was efficiently prepared by the standard Fmoc solid phase synthesis. Tandem mass spectrometric analysis of the obtained conjugates has shown the specific fragmentation pattern during MS/MS experiment. The obtained cryptandic quaternary ammonium group undergoes the Hofmann elimination during collision‐induced dissociation fragmentation followed by the ethoxyl group elimination. The presented quaternization of cryptands by iodoacetylated peptides is relatively easy and compatible with standard solid‐phase peptide synthesis. Additionally, the applicability of such peptide derivatives and their isotopologues selectively deuterated at the α‐carbon in the quantitative LC‐MS analysis was analyzed. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.