Chemical cross-linking with NHS esters

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Author(s) Mädler, Stefanie, Bich, Claudia, Touboul, David, Zenobi, Renato
Publication Type Journal Items, Publication Status: Published
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Title Chemical cross-linking with NHS esters
Subtitle A systematic study on amino acid reactivities
Author(s) Mädler, Stefanie
Bich, Claudia
Touboul, David
Zenobi, Renato
Journal or Series Title Journal of mass spectrometry
Volume Number 44
Issue Number 5
Start Page 694
End Page 706
ISSN 1076-5174
Publisher Wiley
Publication Place Chichester
Publication Date 2009
Keyword(s) chemical cross-linking
NHS ester
amino acids
disuccinimidyl suberate
Abstract Structure elucidation of tertiary or quaternary protein structures by chemical cross-linking and mass spectrometry (MS) has recently gained importance. To locate the cross-linker modification, dedicated software is applied to analyze the mass or tandem mass spectra (MS/MS). Such software requires information on target amino acids to limit the data analysis time. The most commonly used homobifunctional N-hydroxy succinimide (NHS) esters are often described as reactive exclusively towards primary amines, although side reactions with tyrosine and serine have been reported. Our goal was to systematically study the reactivity of NHS esters and derive some general rules for their attack of nucleophilic amino acid side chains in peptides. We therefore studied the cross-linking reactions of synthesized and commercial model peptides with disuccinimidyl suberate (DSS). The first reaction site in all cases was expectedly the alpha-NH2-group of the N-terminus or the epsilon-NH2-group of lysine. As soon as additional cross-linkers were attached or loops were formed, other amino acids were also involved in the reaction. In addition to the primary amino groups, serine, threonine and tyrosine showed significant reactivity due to the effect of neighboring amino acids by intermediate or permanent Type-1 cross-link formation. The reactivity is highly dependent on the pH and on adjacent amino acids.
DOI 10.1002/jms.1544
Additional Notes Received 27 June 2008, Accepted 16 November 2008, Published online 8 January 2009
Document Type Article
Publication Status Published
Language English
Assigned Organisational Unit(s) 03430
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NEBIS System Number 001410098
Source Database ID PP-51481
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  author = "M{\"{a}}dler, Stefanie and Bich, Claudia and Touboul, David and Zenobi, Renato",
  title = "{C}hemical cross-linking with {N}{H}{S} esters: {A} systematic study on amino acid reactivities",
  journal = "Journal of mass spectrometry",
  year = 2009,
  volume = "44",
  number = "5",
  pages = "694--706",

E-Citations record created: Wed, 23 Jun 2010, 20:48:31 CET