| FRYCÁK, Petr, Zbynek ZDRÁHAL, Jitka ULRICHOVÁ, Wolfgang WIEGREBE and Karel LEMR. Evidence of covalent interaction of fumaric acid esters with sulfhydryl groups in peptides. Journal of Mass Spectrometry. John Wiley & Sons, Ltd., 2005, vol. 40, No 10, p. 1309-1318. ISSN 1076-5174. |
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@article{615024,
author = {Frycák, Petr and Zdráhal, Zbynek and Ulrichová, Jitka and Wiegrebe, Wolfgang and Lemr, Karel},
article_number = {10},
keywords = {mass spectrometry; fumarates; cysteine; peptides with sulfhydryl group; identification of covalent interaction},
language = {eng},
issn = {1076-5174},
journal = {Journal of Mass Spectrometry},
title = {Evidence of covalent interaction of fumaric acid esters with sulfhydryl groups in peptides},
volume = {40},
year = {2005}
}
TY - JOUR
ID - 615024
AU - Frycák, Petr - Zdráhal, Zbynek - Ulrichová, Jitka - Wiegrebe, Wolfgang - Lemr, Karel
PY - 2005
TI - Evidence of covalent interaction of fumaric acid esters with sulfhydryl groups in peptides
JF - Journal of Mass Spectrometry
VL - 40
IS - 10
SP - 1309-1318
EP - 1309-1318
PB - John Wiley & Sons, Ltd.
SN - 10765174
KW - mass spectrometry
KW - fumarates
KW - cysteine
KW - peptides with sulfhydryl group
KW - identification of covalent interaction
N2 - Fumaric acid esters, namely dimethylfumarate, have been used for the treatment of psoriasis for many years. Still, their mode of action is not fully clear. Because addition of nucleophiles to the double bonds of fumarates can occur (Michael analogous addition), a study of the interaction of fumarates with cysteine and cysteine-containing peptides possessing nucleophilic sulfhydryl group was carried out. Experiments were performed in aqueous medium at pH7.4 and at 37 C to simulate physiological conditions. It was proven by mass spectrometric measurements using an ion-trap and time-of-flight instrument that a covalent bond can form between fumarates and the sulfhydryl group of cysteine or cysteinyl residues in peptides. Structures of the interaction products were elucidated by multistage mass spectrometry applying collision-induced dissociation. Higher reactivity of dimethylfumarate in comparison to monomethylfumarate and fumaric acid was observed.
ER -
FRYCÁK, Petr, Zbynek ZDRÁHAL, Jitka ULRICHOVÁ, Wolfgang WIEGREBE and Karel LEMR. Evidence of covalent interaction of fumaric acid esters with sulfhydryl groups in peptides. \textit{Journal of Mass Spectrometry}. John Wiley \&{} Sons, Ltd., 2005, vol.~40, No~10, p.~1309-1318. ISSN~1076-5174.
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