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Liquid secondary ion mass spectra of 2‐iminothiolane derivatives
Author(s) -
Bartlett Michael G.,
Busch Kenneth L.
Publication year - 1994
Publication title -
biological mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1052-9306
DOI - 10.1002/bms.1200230609
Subject(s) - chemistry , derivatization , peptide , mass spectrometry , chromatography , derivative (finance) , maleimide , reagent , organic chemistry , biochemistry , financial economics , economics
The derivatization reaction of 2‐iminothiolane with several small peptides has been studied using liquid secondary ion mass spectrometry. The 2‐iminothiolane reagent reacts with side‐chain amino groups and with N‐terminal amines in peptides. Addition of 2‐iminothiolane introduces a free sulfhydryl group and an immonium group into the peptide. The signal intensity for the derivative of a small peptide is approximately the same as that of the [M + H] + ion of the same underivatized peptide from a glycerol solution. The pattern of dissociation observed in the product ion MS/MS spectrum is altered to reflect the derivative. The sulfhydryl group introduced via 2‐iminothiolane reaction further allows for the incorporation of maleimide fluorophores into the peptide for sensitive detection by ultraviolet/visible absorption or fluorescence. This work also reports a previously unrecognized recyclization side‐reaction that involves loss of the immonium group during the derivatization reaction.