Selective acylation of primary amines in peptides and proteins

Journal of Proteome Research

Volumn 6, Issue 12, 2007, Pages 4770-4776

  Abello, Nicolas ^a   Kerstjens, Huib A M ^a   Postma, Dirkje S ^a   Bischoff, Rainer ^a  

^a UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

Author keywords

Acetylation; Acylation; Hydroxylamine; Liquid chromatography; Mass spectrometry; N hydroxysuccinimide; NHS acetate; O acylation

Indexed keywords

AMINE; AMINO ACID; ESTER; HYDROXYL GROUP; WATER;

ACETYLATION; ACYLATION; ARTICLE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEOMICS;

ACYLATION; AMINES; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HORSES; PEPTIDES; PROTEINS; TANDEM MASS SPECTROMETRY;

EID: 38049011270     PISSN: 15353893     EISSN: None     Source Type: Journal    
DOI: 10.1021/pr070154e     Document Type: Article

References (46)

1. Anderson, G. W.; Zimmerman, J. E.; Callahan, F. M. N-hydroxysuccinimide ester in peptide synthesis. J. Am. Chem. Soc. 1963, 85 (19), 3039.
2. Anderson, G. W.; Zimmerman, J. E.; Callahan, F. M. The use of N-hydroxysuccinimide esters in peptide synthesis. J. Am. Chem. Soc. 1964, 86 (9), 1839-1842.
3. Cline, G. W.; Hanna, S. B. Kinetics and mechanisms of the aminolysis of N-hydroxysuccinimide esters in aqueous buffers. J. Org. Chem. 1988, 53, 3583-3586.
4. Hoang, V. M.; Conrads, T. P.; Veenstra, T. D.; Blonder, J.; Terunuma, A.; Vogel, J. C.; Fisher, R. J. Quantitative proteomics employing primary amine affinity tags. J. Biomol. Tech. 2003, 14 (3), 216-223.
5. Kvaratskhelia, M.; Miller, J. T.; Budihas, S. R.; Pannell, L. K.; Le Grice, S. F. Identification of specific HIV-1 reverse transcriptase contacts to the viral RNA:tRNA complex by mass spectrometry and a primary amine selective reagent. Proc. Natl. Acad. Sci. U.S.A. 2002, 99 (25), 15988-15993.
6. Siezen, R. J.; Coppin, C. M.; Benedek, G. B. Permanent suppression of phase separation cataract in calf lens using amine modification agents. Biochem. Biophys. Res. Commun. 1985, 133 (1), 239-247.
7. Yem, A. W.; Zurcher-Neely, H. A.; Richard, K. A.; Staite, N. D.; Heinrikson, R. L.; Deibel, M. R. Jr., Biotinylation of reactive amino groups in native recombinant human interleukin-1 beta. J. Biol. Chem. 1989, 264 (30), 17691-17697.
8. Becker, J. M.; Wilchek, M. Inactivation by avidin of biotin-modified bacteriophage. Biochim. Biophys. Acta 1972, 264 (1), 165-170.
9. Becker, J. M.; Wilchek, M.; Katchalski, E. Irreversible inhibition of biotin transport in yeast by biotinyl-p-nitrophenyl ester. Proc. Natl. Acad. Sci. U.S.A. 1971, 68 (10), 2604-2607.
10. Yang, W. C.; Mirzaei, H.; Liu, X.; Regnier, F. E. Enhancement of amino acid detection and quantification by electrospray ionization mass spectrometry. Anal. Chem. 2006, 78 (13), 4702-4708.
11. Mirzaei, H.; Regnier, F. Enhancing electrospray ionization efficiency of peptides by derivatization. Anal. Chem. 2006, 78 (12), 4175-4183.
12. Ji, T. H.; Ji, I. Macromolecular photoaffinity labeling with radioactive photoactivable heterobifunctional reagents. Anal. Biochem. 1982, 121 (2), 286-289.
13. Ross, P. L.; Huang, Y. N.; Marchese, J. N.; Williamson, B.; Parker, K.; Hattan, S.; Khainovski, N.; Pillai, S.; Dey, S.; Daniels, S.; Purkayastha, S.; Juhasz, P.; Martin, S.; Bartlet-Jones, M.; He, F.; Jacobson, A.; Pappin, D. J. Multiplexed protein quantitation in Saccharomyces cerevisiae using amine-reactive isobaric tagging reagents. Mol. Cell. Proteomics 2004, 3 (12), 1154-1169.
14. Aggarwal, K.; Choe, L. H.; Lee, K. H. Shotgun proteomics using the iTRAQ isobaric tags. Briefings Funct. Genomics Proteomics 2006, 5 (2), 112-120.
15. Zieske, L. R. A perspective on the use of iTRAQ reagent technology for protein complex and profiling studies. J. Exp. Bot. 2006, 57 (7), 1501-1508.
16. Selo, I.; Negroni, L.; Creminon, C.; Grassi, J.; Wal, J. M. Preferential labeling of alpha-amino N-terminal groups in peptides by biotin: application to the detection of specific anti-peptide antibodies by enzyme immunoassays. J. Immunol. Methods 1996, 199 (2), 127-138.
17. Gaudriault, G.; Vincent, J. P. Selective labeling of alpha- or epsilon-amino groups in peptides by the Bolton-Hunter reagent. Peptides 1992, 13 (6), 1187-1192.
18. Nikov, G.; Bhat, V.; Wishnok, J. S.; Tannenbaum, S. R. Analysis of nitrated proteins by nitrotyrosine-specific affinity probes and mass spectrometry. Anal. Biochem. 2003, 320 (2), 214-222.
19. Smith, G. P. Kinetics of amine modification of proteins. Bioconjugate Chem. 2006, 17 (2), 501-506.
20. Smith, J. S.; Miller, B. T.; Knock, S. L.; Kurosky, A. Biotinylated peptides/proteins. I. Determination of stoichiometry of derivatization. Anal. Biochem. 1991, 197 (1), 247-253.
21. Bayer, E. A.; Wilchek, M.; Meir, Wilchek; Edward, A. B. Protein biotinylation. Methods Enzymol. 1990, Volume 184, 138-160.
22. Wilchek, M.; Bayer, E. A. Biotin-containing reagents. Methods Enzymol. 1990, 184, 123-138.
23. Regnier, F. E.; Julka, S. Primary amine coding as a path to comparative proteomics. Proteomics 2006, 6 (14), 3968-3979.
24. Ishikawa, Y.; Yamamoto, Y.; Otsubo, M.; Theg, S. M.; Tamura, N. Chemical modification of amine groups on PS II protein(s) retards photoassembly of the photosynthetic water-oxidizing complex. Biochemistry 2002, 41 (6), 1972-1980.
25. Holmquist, B.; Blumberg, S.; Vallee, B. L. Superactivation of neutral proteases: acylation with N-hydroxysuccinimide esters. Biochemistry 1976, 15 (21), 4675-80.
26. Blumberg, S.; Vallee, B. L. Superactivation of thermolysin by acylation with amino acid N-hydroxysuccinimide esters. Biochemistry 1975, 14 (11), 2410-2419.
27. Miller, B. T. Acylation of peptide hydroxyl groups with the Bolton-Hunter reagent. Biochem. Biophys. Res. Commun. 1996, 218 (1), 377-382.
28. Miller, B. T.; Collins, T. J.; Nagle, G. T.; Kurosky, A. The occurrence of O-acylation during biotinylation of gonadotropin-releasing hormone and analogs. Evidence for a reactive serine. J. Biol. Chem. 1992, 267 (8), 5060-5069.
29. Miller, B. T.; Collins, T. J.; Rogers, M. E.; Kurosky, A. Peptide biotinylation with amine-reactive esters: differential side chain reactivity. Peptides 1997, 18 (10), 1585-1595.
30. Miller, B. T.; Kurosky, A. Elevated intrinsic reactivity of seryl hydroxyl groups within the linear peptide triads His-Xaa-Ser or Ser-Xaa-His. Biochem. Biophys. Res. Commun. 1993, 196 (1), 461-467.
31. Miller, B. T.; Rogers, M. E.; Smith, J. S.; Kurosky, A. Identification and characterization of O-biotinylated hydroxy amino acid residues in peptides. Anal. Biochem. 1994, 219 (2), 240-248.
32. Riordan, J. F.; Vallee, B. L. Acetylation. Methods Enzymol. 1972, 25, 494-499.
33. Washburn, M. P.; Wolters, D.; Yates, J. R. 3rd, Large-scale analysis of the yeast proteome by multidimensional protein identification technology. Nat. Biotechnol. 2001, 19 (3), 242-247.
34. Ling, N. C.; Rivier, J. E.; Monahan, M. W.; Vale, W. W. Analogues of luteinizing hormone releasing factor modified at positions 2, 6, and 10. J. Med. Chem. 1976, 19 (7), 937-941.
35. Meyer, H. E.; Hoffmann-Posorske, E.; Korte, H.; Heilmeyer, L. M. Jr. Sequence analysis of phosphoserine-containing peptides. Modification for picomolar sensitivity. FEBS Lett. 1986, 204 (1), 61-66.
36. Oda, Y.; Nagasu, T.; Chait, B. T. Enrichment analysis of phosphorylated proteins as a tool for probing the phosphoproteome. Nat. Biotechnol. 2001, 19 (4), 379-382.
37. Jaffe, H.; Veeranna; Pant, H. C. Characterization of serine and threonine phosphorylation sites in beta-elimination/ethanethiol addition-modified proteins by electrospray tandem mass spectrometry and database searching. Biochemistry 1998, 37, (/?> (46), 16211-16224.
38. Hanisch, F. G.; Jovanovic, M.; Peter-Katalinic, J. Glycoprotein identification and localization of O-glycosylation sites by mass spectrometric analysis of deglycosylated/alkylaminylated peptide fragments. Anal. Biochem. 2001, 290 (1), 47-59.
39. Mirgorodskaya, E.; Hassan, H.; Clausen, H.; Roepstorff, P. Mass spectrometric determination of O-glycosylation sites using beta-elimination and partial acid hydrolysis. Anal. Chem. 2001, 73 (6), 1263-1269.
40. Ji, T. H.; Ji, I. Heterobifunctional photoaffinity labeling reagents. Pharmacol. Ther. 1989, 43 (3), 321-332.
41. Clementi, C.; Carloni, P.; Maritan, A. Protein design is a key factor for subunit-subunit association. Proc. Natl. Acad. Sci. U.S.A. 1999, 96 (17), 9616-9621.
42. Hestrin, S. The reaction of acetylcholoine and other carboxylic acid derivatives with hydroxylamine and its analytical application. J. Biol. Chem. 1949, 180 (1), 249-261.
43. Schmidt, A.; Kellermann, J.; Lottspeich, F. A novel strategy for quantitative proteomics using isotope-coded protein labels. Proteomics 2005, 5 (1), 4-15.
44. Bornstein, P.; Balian, G. Cleavage at Asn-Gly bonds with hydroxylamine. Methods Enzymol. 1977, 47, 132-145.
45. Canova-Davis, E.; Eng, M.; Mukku, V.; Reifsnyder, D. H.; Olson, C. V.; Ling, V. T. Chemical heterogeneity as a result of hydroxylamine cleavage of a fusion protein of human insulin-like growth factor I. Biochem. J. 1992, 285 (Pt 1), 207-213.
46. Ramachandran, L. K.; Narita, K. Reactions involving the amide and carboxyl groups of tobacco mosaic virus (TMV) protein. Biochim. Biophys. Acta 1958, 30 (3), 616-624.