Peptide sequencing through N-terminal phosphonylation and electrospray ionization mass spectrometry

Journal of Mass Spectrometry

Volumn 40, Issue 6, 2005, Pages 772-776

  Bao, Jiangyin ^a   Ai, Huiwang ^a   Fu, Hua ^a   Jiang, Yuyang ^a   Zhao, Yufen ^a   Huang, Cheng ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

Electrospray ionization mass spectrometry; Ethoxyphenylphosphinate; N terminal phosphonylation; Peptide sequencing; Phosphonamidate peptides

Indexed keywords

AMINES; AMINO ACIDS; IONIZATION; MASS SPECTROMETRY; METHANE; THERMAL EFFECTS;

ELECTROSPRAY; ELECTROSPRAY IONIZATION; PEPTIDE SEQUENCING; PHOSPHONYLATION;

POLYPEPTIDES;

CARBON TETRACHLORIDE; ETHOXYPHENYLPHOSPHINATE; PHOSPHINE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; ELECTROSPRAY MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; TANDEM MASS SPECTROMETRY;

PEPTIDES; PHOSPHONIC ACIDS; SEQUENCE ANALYSIS, PROTEIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 21344439603     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.850     Document Type: Article

References (37)

1. Gygi SP, Aebersold R. Mass spectrometry and proteomics. Curr. Opin. Chem. Biol 2000; 4: 489.
2. Wang P, Arabaci G, Pei D. Rapid sequencing of library-derived peptides by partial Edman degradation and mass spectrometry. J. Comb. Chem. 2001; 3: 251.
3. Barber M, Bordoli RS, Sedgwick RD, Tyler AN, Bycroft BW. Fast atom bombardment mass spectrometry of bleomycin A2 and B2 and their metal complexes. Biochem. Biophy. Res. Commun. 1981; 101: 632.
4. Karas M, Bachmann D, Bahr U, Hillenkamp F. Matrix-assisted ultraviolet laser desorption of non-volatile compounds. Int. J. Mass Spectrom. Ion Proc. 1987; 78: 53.
5. Hillenkamp, F. Laser desorption mass spectrometry: mechanisms, techniques, and applications. Adv. Mass Spectrom. 1989; 11A: 354.
6. Fenn JB, Mann M, Meng CK, Wong SF, Whitehouse CM. Electrospray ionization for mass spectrometry of large biomolecules. Science 1989; 246: 64.
7. Chait BT, Wang R, Beavis RC, Kent SBH. Protein ladder sequencing. Science 1993; 262: 89.
8. Samyn B, Hardeman K, Van der Eycken J, Van Beeumen J. Applicability of the alkylation chemistry for chemical C-terminal protein sequence analysis. Anal. Chem. 2000; 72: 1389.
9. Boyd VL, Bozzini M, Zon G, Noble RL, Mattaliano RJ. Sequencing of peptides and proteins from the carboxy terminus. Anal. Biochem. 1992; 206: 344.
10. Patterson DH, Tarr GE, Regnier FE, Martin SA. C-terminal ladder sequencing via matrix-assisted laser-desorption mass-spectrometry coupled with carboxypeptidase-y time-dependent and concentration-dependent digestions. Anal. Chem. 1995; 67: 3971.
11. Thiede B, Wittmannliebold B, Bienert M, Krause E. Maldi-ms for C-terminal sequence determination of peptides and proteins degraded by carboxypeptidase-y and carboxypeptidase-P. FEBS Lett. 1995; 357: 65.
12. Lee SW, Kim HS, Beauchamp JL. Salt bridge chemistry applied to gas-phase peptide sequencing: Selective fragmentation of sodiated gas-phase peptide ions adjacent to aspartic acid residues. J. Am. Chem. Soc. 1998; 120: 3188.
13. Sundqvist B, Kamensky I, Haakansson P, Kjellberg J, Salehpour M, Widdiyasekera S, Fohlman J, Peterson PA, Roepstorff P. California-252 plasma desorption time of flight mass spectroscopy of proteins. Biomed. Mass Spectrom. 1984; 11: 242.
14. Biemann K. Mass spectrometry of peptides and proteins. Annu. Rev. Biochem. 1992; 61: 977.
15. Mallis LM, Russell DH. Fast atom bombardment-tandem mass spectrometry studies of organo-alkali metal ions of small peptides. Anal. Chem. 1986; 58: 1076.
16. Tang X, Ens W, Standing KG, Westmore JB. Daughter ion mass spectra from cationized molecules of small oligopeptides in a reflecting time-of-flight mass spectrometer. Anal. Chem. 1988; 60: 1791.
17. Renner D, Spiteller G. Linked scan investigation of peptide degradation initiated by liquid secondary ion mass spectrometry. Biomed. Mass Spectrom. 1988; 15: 75.
18. Grese RP, Cerny RL, Gross ML. Metal ion-peptide interactions in the gas phase: a tandem mass spectrometry study of alkali metal cationized peptides. J. Am. Chem. Soc. 1989; 111: 2835.
19. Grese RP, Gross ML. Gas-phase interactions of lithium ions and dipeptides. J. Am. Chem. Soc. 1990; 112: 5098.
20. Lin T, Payne AH, Glish GL. Dissociation pathways of alkalicationized peptides: Opportunities for C-terminal peptide sequencing. J. Am. Soc. Mass Spectrom. 2001; 12: 497.
21. Teesch LM, Adams J. Intrinsic interactions between alkaline earth metal ions and peptides: a gas-phase study. J. Am. Chem. Soc. 1990; 112: 4110.
22. Teesch LM, Adams J. Fragmentations of gas-phase complexes between alkali metal ions and peptides: metal ion binding to carbonyl oxygens and other neutral functional groups. J. Am. Chem. Soc. 1991; 113: 812.
23. Lin T, Glish GL. C-Terminal Peptide Sequencing via Multistage Mass Spectrometry. Anal. Chem. 1998; 70: 5162.
24. Lee S-W, Kim HS, Beauchamp JL. Salt Bridge Chemistry Applied to Gas-Phase Peptide Sequencing: Selective Fragmentation of Sodiated Gas-Phase Peptide Ions Adjacent to Aspartic Acid Residues. J. Am. Chem. Soc. 1998; 120: 3188.
25. Li HB, Siu KWM, Guevremont R, LeBlanc JCY. Complexes of silver(I) with peptides and proteins as produced in electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 1997; 8: 781.
26. Gonzalez J, Besada V, Garay H, Reyes O, Padron G, Tambara Y, Takao T, Shimonishi Y. Effect of the position of a basic amino acid on C-terminal rearrangement of protonated peptides upon collision-induced dissociation. J. Mass Spectrom. 1996; 31: 150.
27. Nemirovskiy OV, Gross ML. Complexes of iron (U) with cysteine-containing peptides in the gas phase. J. Am. Soc. Mass Spectrom. 1996; 7: 977.
28. Newton KA, McLuckey SA. Generation and manipulation of sodium cationized peptides in the gas phase. J. Am. Soc. Mass Spectrom. 2004; 15: 607.
29. Marner OA, Just G, Li CS, Preville P, Watson S, Young R, Yergey JA. Enhancement of mass-spectrometric detection of Itc4, Itd4, and Ite4 by derivatization. J. Am. Soc. Mass Spectrom. 1994; 5: 292.
30. Huang ZH, Wu J, Roth KDW, Yang Y, Gage DA, Watson JT. A Picomole-Scale Method for Charge Derivatization of Peptides for Sequence Analysis by Mass Spectrometry. Anal. Chem. 1997; 69: 137.
31. Keough T, Youngquist RS, Lacey MP. A method for high-sensitivity peptide sequencing using postsource decay matrix-assisted laser desorption ionization mass spectrometry. Proc. Natl. Acad, Sci. USA 1999; 96: 7131.
32. Lindh I, Sjövall J, Bergman T, Griffiths WJ. Negative-ion electrospray tandem mass spectrometry of peptides derivatized with 4-aminonaphthalenesulphonic acid. J. Mass spectrum. 1998; 33: 988.
33. Chen J, Chen Y, Gong P, Jiang Y, Li YM, Zhao YF. Novel phosphoryl derivatization method for peptide sequencing by electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2002; 16: 531.
34. Chai WG, Yan L, Wang GH, Liang XY, Zhao YF, Ji GJ. Improvement in sensitivity of fast atom bombardment mass spectrometry of amino acids by di-isopropylphosphorylation. Biomed. Environ. Mass Spectrom. 1987; 14: 331.
35. Ai HW, Fu H, Zhao YF. Novel synthetic method of phosphonamidate peptides and its application in peptide sequencing via multistage mass spectrometry. Chem. Commun. 2003; 2724.
36. Tsaprailis G, Somogyi A, Nikolaev EN, Wysocki VH. Refining the model for selective cleavage at acidic residues in arginine-containing protonated peptides. Int. J. Mass. Spectrom. 2000; 195: 467.
37. Gu CG, Tsaprailis G, Breci L, Wysocki VH. Selective gas-phase cleavage at the peptide bond terminal to aspartic acid in fixed-charge derivatives of asp-containing peptides. Ana. Chem. 2000; 72: 5804.