Structure characterization of functional histidine residues and carbethoxylated derivatives in peptides and proteins by mass spectrometry

Bioconjugate Chemistry
M KalkumM O Glocker

Abstract

We developed a mass spectrometric method to precisely characterize the structures of the diethyl pyrocarbonate (DEP)-modified amino acid derivatives in intact peptides and proteins. Using acetate-buffered solutions for modification reactions improved the yields of DEP modification. UV quantification of carbethoxylation of angiotensin II was consistent with the degree of mass spectrometrically determined modification. Unequivocal identification of the modification sites in carbethoxylated angiotensin II derivatives was achieved by HPLC separation and mass spectrometric sequencing. With increasing concentrations of DEP, a gradual increase of carbethoxy groups, comprising biscarbethoxylation products, was detected in angiotensin II and in insulin. When using a high molar excess of DEP, histidine carbethoxylation was found together with modifications at alpha-amino groups and tyrosine residues. The sites of carbethoxylation in insulin were identified by MALDI-MS-peptide mapping analyses of the tryptic digestion mixtures from the nonreduced insulin derivatives and after reduction of disulfide bonds, demonstrating that histidine carbethoxylation was sufficiently stable during disulfide bond reduction and tryptic digestion at pH 7.5. ...Continue Reading

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Citations

Feb 3, 2012·Journal of the American Society for Mass Spectrometry·Yuping Zhou, Richard W Vachet
Feb 22, 2012·Journal of the American Society for Mass Spectrometry·Yuping Zhou, Richard W Vachet
May 29, 2000·Biochimica Et Biophysica Acta·A L PerraudR Gross
Jun 15, 2007·Analytical Biochemistry·Xiaohui LiuJames P Reilly
Nov 19, 2008·Mass Spectrometry Reviews·Vanessa Leah Mendoza, Richard W Vachet
Sep 29, 2004·Biochemical and Biophysical Research Communications·Jirí SantrůcekMilan Kodícek
Mar 15, 2018·Annual Review of Biophysics·Janna Kiselar, Mark R Chance
Mar 30, 2001·The Journal of Biological Chemistry·R J HondalR F Burk
Feb 3, 2004·The Journal of Biological Chemistry·Tali GidalevitzYair Argon
Sep 3, 2009·Inorganic Chemistry·Yamini P Ginotra, Prasad P Kulkarni
Aug 8, 2009·Journal of Proteome Research·Xiaohui Liu, James P Reilly
Mar 15, 2008·Analytical Chemistry·Vanessa Leah Mendoza, Richard W Vachet
Apr 5, 2019·Journal of Chemical Theory and Computation·Melanie L Aprahamian, Steffen Lindert
Nov 4, 2006·Journal of Proteome Research·Richard L BeardsleyJames P Reilly
Jul 17, 1999·Analytical Chemistry·C K LariveS Bogdanowich-Knipp
Dec 22, 2021·Analytical Chemistry·Catherine Y TremblayRichard W Vachet
Dec 29, 2021·Analytical Chemistry·Xiao PanRichard W Vachet

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