Protein cross-links: Universal isolation and characterization by isotopic derivatization and electrospray ionization mass spectrometry

Analytical Biochemistry

Volumn 273, Issue 2, 1999, Pages 192-203

  Chen, X ^a   Yong Hong Chen, ^a   Anderson, V E ^a  

^a CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Crosslink; Dinitrofluorobenzene; Disulfide; Electrospray mass spectrometry; HPLC, ubiquitin; Peptide sequencing

Indexed keywords

AMINO ACIDS; CHROMATOGRAPHY; CROSSLINKING; ISOTOPES; MASS SPECTROMETRY; PEPTIDES; SULFUR COMPOUNDS;

DINITROFLUOROBENZENE; DISULFIDE; ELECTROSPRAY MASS SPECTROMETRY; PEPTIDE SEQUENCING; UBIQUITIN;

ELECTROSPRAY IONIZATION;

1 FLUORO 2,4 DINITROBENZENE; 2,4 DINITROPHENOL; LYSINE DERIVATIVE; PROTEIN;

ARTICLE; CHEMICAL MODIFICATION; CROSS LINKING; HYDROLYSIS; ISOTOPE LABELING; MASS SPECTROMETRY; MOLECULAR DYNAMICS; PRIORITY JOURNAL; PROTEIN DETERMINATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEQUENCE ANALYSIS;

EID: 0033543508     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1006/abio.1999.4243     Document Type: Article

References (23)

1. D.R. Sell V.M. Monnier Structure elucidation of a senescence cross-link from human extracellular matrix. Implication of pentoses in the aging process J. Biol. Chem. 264 1989 21597 21602
2. J.W. Baynes Role of oxidative stress in development of complications in diabetes Diabetes 40 1991 405 412
3. N. Ito S.E. Phillips C. Stevens Z.B. Ogel M.J. McPherson J.N. Keen K.D. Yadav P.F. Knowles Novel thioether bond revealed by a 1.7 A crystal structure of galactose oxidase Nature 350 1991 87 90
4. W.S. McIntire D.E. Wemmer A. Chistoserdov M.E. Lidstrom A new cofactor in a prokaryotic enzyme: Tryptophan tryptophylquinone as the redox prosthetic group in methylamine dehydrogenase Science 252 1991 817 824
5. A.L. Haas T.J. Siepmann Pathways of ubiquitin conjugation FASEB J. 11 1997 1257 1268
6. C.M. Pickart Targeting of substrates to the 26S proteasome FASEB J. 11 1997 1055 1066
7. R.H. Nagaraj I.N. Shipanova F.M. Faust Protein cross-linking by the Maillard reaction. Isolation, characterization, and in vivo detection of a lysine-lysine cross-link derived from methylglyoxal J. Biol. Chem. 271 1996 19338 19345
8. J.R. Requena M.X. Fu M.U. Ahmed A.J. Jenkins T.J. Lyons J.W. Baynes S.R. Thorpe Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein Biochem. J. 322 1997 317 325
9. D. Mornet K. Ue P. Chaussepied M.F. Morales Modification of the actin interface of skeletal myosin subfragment-1 by treatment with dibromobimane Eur. J. Biochem. 159 1986 555 561
10. X. Chen D. Eswaran M.A. Smith G. Perry V.E. Anderson Universal isolation of cross-linked peptides: Application to neurofibrillary tangles Bioconj. Chem. 10 1998 112 118
11. S.H. De Bruin E. Bucci Reaction of 1-fluoro-2,4-dinitrobenzene with the free alpha chains of human hemoglobin. Evaluation of the pK of the terminal amino group J. Biol. Chem. 246 1971 5228 5233
12. E.J. Neer W. Konigsberg The characterization of modified human hemoglobin. II. Reaction with 1- fluoro-2,4-dinitrobenzene J. Biol. Chem. 243 1968 1966 1970
13. S. Van Nocker R.D. Vierstra Cloning and characterization of a 20-kDa ubiquitin carrier protein from wheat that catalyzes multiubiquitin chain formation in vitro Proc. Natl. Acad. Sci. USA 88 1991 10297 10301
14. 3(50%)]-2,4-dinitrofluorobenzene J. Am. Soc. Mass Spectrom. 10 1999 448 452
15. S. Shaltiel Thiolysis of some dinitrophenyl derivatives of amino acids Biochem. Biophys. Res. Commun. 29 1967 178 183
16. N.S. Kosower E.M. Kosower B. Wertheim W.S. Correa Diamide, a new reagent for the intracellular oxidation of glutathione to the disulfide Biochem. Biophys. Res. Commun. 37 1969 593 596
17. S. Udenfriend S. Stein P. Bohlen W. Dairman W. Leimgruber M. Weigele Fluorescamine: A reagent for assay of amino acids, peptides, proteins, and primary amines in the picomole range Science 178 1972 871 872
18. N. Jentoft D.G. Dearborn Protein labeling by reductive alkylation Methods Enzymol. 91 1983 570 579
19. R.G. Duggleby H. Kaplan A competitive labeling method for the determination of the chemical properties of solitary functional groups in proteins Biochemistry 14 1975 5168 5175
20. A. Niederwieser Adsorption of neutral polystyrene resin. A simple method for extraction of 2,4-dinitrophenyl derivatives from aqueous solution and for decoloration of protein hydrolysates J. Chromatogr. 54 1971 215 223
21. R. Foster Organic Charge Transfer Complexes 1969 Academic Press New York
22. M.J. Huddleston M.F. Bean S.A. Carr Collisional fragmentation of glycopeptides by electrospray ionization LC/MS and LC/MS/MS: methods for selective detection of glycopeptides in protein digests Anal. Chem. 65 1993 877 884
23. B.T. Chait R. Wang R.C. Beavis S.B. Kent Protein ladder sequencing Science 262 1993 89 92