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Mass spectrometry of synthetic oligopeptides N , O ‐permethylated, N ‐acetylated derivatives
Author(s) -
Haegele K. D.,
Holzer G.,
Parr W.,
Nakagawa S. H.,
Desiderio D. M.
Publication year - 1974
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200010307
Subject(s) - chemistry , amide , acetylation , oligopeptide , peptide , mass spectrometry , stereochemistry , amino acid , organic chemistry , biochemistry , chromatography , gene
Mass spectra of a series of stable isotope derivatives aided a structure elucidation study of an amino acid amide (Tyr‐NH 2 ) and the following family of synthetic oligopeptides: Gly‐Tyr‐NH 2 , Gly‐Gly‐Tyr‐NH 2 , Gln‐Gly‐Gly‐Tyr‐NH 2 , Gln‐Gln‐Gly‐Gly‐Tyr‐NH 2 , Ala‐Gln‐Gln‐Gly‐Gly‐Tyr‐NH 2 , Ser‐Ala‐Gln‐Gln‐Gly‐Gly‐Tyr‐NH 2 and Lys‐Ser‐Ala‐Gln‐Gln‐Gly‐Gly‐Tyr‐NH 2 . This series of peptides was synthesized by classical methods. N , O ‐permethylated, N ‐acetylated derivatives were synthesized to provide sufficient volatility for mass spectrometry. Various combinations of stable isotope derivatives (CH 3 CO + CH 3 , CD 3 CO + CH 3 , CH 3 CO + CD 3 , CD 3 CO + CD 3 ) confirmed proposed fragmentation pathways and corroborated hypothetical ion structures. This family of oligopeptides corresponds to the C‐terminus of scotophobin.