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Diagonal chromatographic selection of cysteinyl peptides modified with benzoquinones

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Abstract

The derivatization of cysteine-containing peptides with benzoquinone compounds is rapid, quantitative and specific in acidic media. The conversion of cysteines into hydrophobic benzoquinone-adducted residues in peptides is used here to alter the chromatographic properties of cysteinyl peptides during liquid chromatography separation. The benzoquinone derivatization is shown to allow the accurate selection of cysteine-containing peptides of bovine serum albumin tryptic digest by diagonal reversed-phase chromatography, which consists of one primary and a series of secondary identical liquid chromatographic separations, before and after a cysteinyl-targeted modification of the peptides by benzoquinone compounds.

Diagonal chromatographic selection of cysteinyl peptides modified with benzoquinones

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References

  1. Gygi SP, Rist B, Gerber SA, Turecek F, Gelb MH, Aebersold R (1999) Nat Biotechnol 17:994–999

    Article  CAS  Google Scholar 

  2. Brown JR, Hartley BS (1966) Biochem J 101:214–228

    CAS  Google Scholar 

  3. Butler PJG, Harris JI, Hartley BS, Leberman R (1967) Biochem J 103:P78–P79

    Google Scholar 

  4. Tang J, Hartley BS (1967) Biochem J 102:593–599

    CAS  Google Scholar 

  5. Cruickshank WH, Radhakrishnan TM, Kaplan H (1971) Can J Biochem 49:1225–1232

    Article  CAS  Google Scholar 

  6. Cruickshank WH, Malchy BL, Kaplan H (1974) Can J Biochem 52:1013–1017

    Article  CAS  Google Scholar 

  7. Gevaert K, Van Damme P, Ghesquiere B, Vandekerckhove J (2006) BBA–Proteins Proteomics 1764:1801–1810

    Google Scholar 

  8. Gevaert K, Van Damme P, Martens L, Vandekerckhove J (2005) Anal Biochem 345:18–29

    Article  CAS  Google Scholar 

  9. Gevaert K, Ghesquiere B, Staes A, Martens L, Van Damme J, Thomas GR, Vandekerckhove J (2004) Proteomics 4:897–908

    Article  CAS  Google Scholar 

  10. Gevaert K, Van Damme J, Goethals M, Thomas GR, Hoorelbeke B, Demol H, Martens L, Puype M, Staes A, Vandekerckhove J (2002) Mol Cell Proteomics 1:896–903

    Article  CAS  Google Scholar 

  11. Gevaert K, Goethals M, Martens L, Van Damme J, Staes A, Thomas GR, Vandekerckhove J (2003) Nat Biotechnol 21:566–569

    Article  CAS  Google Scholar 

  12. Liu PR, Feasley CL, Regnier FE (2004) J Chromatogr A 1047:221–227

    Article  CAS  Google Scholar 

  13. Gevaert K, Staes A, Van Damme J, De Groot S, Hugelier K, Demol H, Martens L, Goethals M, Vandekerckhove J (2005) Proteomics 5:3589–3599

    Article  CAS  Google Scholar 

  14. Ghesquiere B, Van Damme J, Martens L, Vandekerckhove J, Gevaert K (2006) J Proteome Res 5:2438–2447

    Article  CAS  Google Scholar 

  15. Mason DE, Liebler DC (2000) Chem Res Toxicol 13:976–982

    Article  CAS  Google Scholar 

  16. Hansen BT, Jones JA, Mason DE, Liebler DC (2001) Anal Chem 73:1676–1683

    Article  CAS  Google Scholar 

  17. Roussel C, Dayon L, Jensen H, Girault HH (2004) J Electroanal Chem 570:187–199

    Article  CAS  Google Scholar 

  18. Dayon L, Abonnenc M, Prudent M, Lion N, Girault HH (2006) J Mass Spectrom 41:1484–1490

    Article  CAS  Google Scholar 

  19. Digga A, Gracheva S, Livingstone C, Davis J (2003) Electrochem Commun 5:732–736

    Article  CAS  Google Scholar 

  20. Cech ND, Krone JR, Enke CG (2001) Anal Chem 73:208–213

    Article  CAS  Google Scholar 

  21. Sechi S, Chait BT (1998) Anal Chem 70:5150–5158

    Article  CAS  Google Scholar 

  22. Gevaert K, Pinxteren J, Demol H, Hugelier K, Staes A, Van Damme J, Martens L, Vandekerckhove J (2006) J Proteome Res 5:1415–1428

    Article  CAS  Google Scholar 

  23. Horth P, Miller CA, Preckel T, Wenz C (2006) Mol Cell Proteomics 5:1968–1974

    Article  CAS  Google Scholar 

  24. Michel PE, Crettaz D, Morier P, Heller M, Gallot D, Tissot JD, Reymond F, Rossier JS (2006) Electrophoresis 27:1169–1181

    Article  CAS  Google Scholar 

  25. Xu CF, Wang HB, Li DM, Kong XP, Neubert TA (2007) Anal Chem 79:2007–2014

    Article  CAS  Google Scholar 

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Acknowledgement

This work was supported by a Swiss National Science Fundation grant entitled “Development of new analytical tools for proteomics” (Grant No 200020-105489). The Ecole Polytechnique Fédérale de Lausanne is thanked for its financial support in the acquisition of the LC Packings Ultimate™ system. Mélanie Abonnenc and Dr. Niels Lion are thanked for their expertise in LC ESI–MS and very fruitful discussions.

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  1. Loïc Dayon

    Present address: Biomedical Proteomics Research Group, Department of Structural Biology and Bioinformatics, Faculty of Medicine, University of Geneva, Geneva, Switzerland

Authors and Affiliations

  1. Laboratoire d’Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 6, 1015, Lausanne, Switzerland

    Loïc Dayon & Hubert H. Girault

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  1. Loïc Dayon
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  2. Hubert H. Girault
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Correspondence to Hubert H. Girault.

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Dayon, L., Girault, H.H. Diagonal chromatographic selection of cysteinyl peptides modified with benzoquinones. Anal Bioanal Chem 389, 841–849 (2007). https://doi.org/10.1007/s00216-007-1492-8

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  • DOI: https://doi.org/10.1007/s00216-007-1492-8

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