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Inne
Synthesis and mass spectrometry analysis of quaternary cryptando-peptidic conjugates.
Autorzy
Rok wydania
2015
Czasopismo
Numer woluminu
21
Strony
879-886
DOI
10.1002/psc.2830
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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.
Słowa kluczowe
cryptands, fixed charge tags, ESI-MS/MS, HDX, quantitative analysis
Adres publiczny
http://dx.doi.org/10.1002/psc.2830
Strona internetowa wydawcy
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