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Mass spectrometric characterization of Amadori compounds related to the opioid peptide morphiceptin
Author(s) -
Žigrović Ivanka,
Versluis Cornelis,
Horvat Štefica,
Heerma Wigger
Publication year - 1998
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(19980227)12:4<181::aid-rcm136>3.0.co;2-v
Subject(s) - chemistry , amadori rearrangement , molecule , ion , mass spectrum , polyatomic ion , peptide , stereochemistry , dissociation (chemistry) , medicinal chemistry , organic chemistry , biochemistry , glycation , receptor
The high‐energy collision‐induced dissociation (CID) spectra of synthesized Amadori compounds, related to the exogenous opioid peptide morphiceptin, have been investigated. The spectra of [M + H] + ions of protected, partially protected and unprotected Amadori compounds exhibit mainly A‐ and Y″‐type sequence ions. The protected compounds show peaks corresponding to the elimination of a C 3 H 6 O molecule, characteristic of a protecting isopropylidene group at the saccharide moiety. The position of the isopropylidene group in the partially protected Amadori compound has been derived from the CID spectrum of its [M + Na] + ion. A two‐bond cross‐ring cleavage reaction generates an ion at m/z 656, corresponding to the loss of a 90 Da neutral (C 3 H 6 O 3 ), and must originate from the C2‐C3 isopropylidene‐protected Amadori compound. The most intense ions in the CID spectrum of the [M + H] + ion of the unprotected Amadori compound arise from losses of water molecules. Comparison of the CID spectra of the [M + H] + ions of Amadori compounds with that for the parent peptide morphiceptin revealed a preferential A 1 ‐ion formation for Amadori compounds. © 1998 John Wiley & Sons, Ltd.