Mass spectrometric differentiation of α- and β-aspartic acid in a pseudo-tetrapeptide thrombosis inhibitor and its isomer

European Journal of Mass Spectrometry

Volumn 10, Issue 2 SPEC. ISS., 2004, Pages 279-287

  Luu, Nganha C ^a,c   Robinson, Scott ^a   Zhao, R ^b   McKean, R ^b   Ridge, Douglas P ^a  

^a UNIVERSITY OF DELAWARE   (United States)

^b SANOFI   (France)

^c DUPONT COMPANY   (United States)

Author keywords

Aspartic acid isomers; Energy dependence of SORI CID; ESI; FT MS; SORI CID; Thrombosis inhibitor

Indexed keywords

ALPHA ASPARTIC ACID; ANTICOAGULANT AGENT; ASPARTIC ACID DERIVATIVE; ISOASPARTIC ACID; TETRAPEPTIDE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; DECOMPOSITION; ELECTROSPRAY MASS SPECTROMETRY; ENERGY; MASS SPECTROMETRY; MOLECULAR INTERACTION; PROTEIN DEGRADATION; PROTON TRANSPORT;

ASPARTIC ACID; ISOASPARTIC ACID; ISOMERISM; KINETICS; MOLECULAR STRUCTURE; OLIGOPEPTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; THROMBOSIS;

EID: 1942467953     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.634     Document Type: Conference Paper

References (25)

1. M.C. Manning, K. Patel and R.T. Borchardt, "Stability of Protein Pharmaceuticals," Pharm. Res. 6, 903 (1989).
2. C. Oliyai, C. Schoneich, G.S. Wilson and R.T. Borchardt, "Chemical and Physical Stability of Protein Pharmaceuticals", in Topics in Pharmaceutical Sciences. Medpharm Scientific, Stuttgard, Germany (1991).
3. T.J. Ahren and M.C. Manning (Eds), Stability of Protein Pharmaceuticals: Part A. Chemical and Physical Pathways of Protein Degradation. Plenum Press, New York, USA (1992).
4. T.J. Ahren and M.C. Manning (Eds), Stability of Protein Pharmaceuticals: Part B. In Vivo Pathways of Degradation and Strategies for Protein Stabilization. Plenum Press, New York, USA (1992).
5. L.E. Kirsch, R.M. Molloy, M. Debono, P. Baker and K.Z. Farid, "Kinetics of the aspartyl transpeptidation of daptomycin, a novel lipopeptide antibiotic," Pharm. Res. 6, 387 (1989).
6. G. Perseo, R. Forino, M. Galantino, B. Gioia, V. Malatesta and R. DeCastiglione, Int. J. Peptide Protein Res. 27, 51 (1986).
7. I.M. Ota and S. Clarke, "Calcium affects the spontaneous degradation of aspartyl/asparaginyl residues in calmodulin," Biochemistry 28, 4020 (1989).
8. T. Tsuda, M. Uchiyama, T. Sato, H. Yoshito, Y. Tsuchiya, S. Ishikawa, M. Ohmae, S. Watanabe and Y. Miyake, "Mechanism and kinetics of secretin degradation in aqueous solutions," J. Pharm. Sci. 79, 223 (1990).
9. C. George-Nascimento, J. Lowenson, M. Borissenko, M. Calderon, A. Medina-Selby, J. Kuo, S. Clarke and A. Randolph, "Replacement of a labile aspartyl residue increases the stability of human epidermal growth factor," Biochemistry 29, 9584 (1990).
10. F. Marcus, "Preferential cleavage at aspartyl-prolyl peptide bonds in dilute acid," Int. J. Peptide Protein Res. 25, 542 (1985).
11. S.A. Inglis, Methods Enzymol. 91, 324 (1983).
12. C. Oliyai and R. Borchardt, "Chemical pathways of peptide degradation. IV. Pathways, kinetics, and mechanism of degradation of an aspartyl residue in a model hexapeptide," Pharm. Res. 10, 95 (1993).
13. L.J. Gonzalez, T. Shimizu, Y. Satomi, L. Betancourt, B. Vladimir, P. Orlando, R. Gabriel, T. Shirasawa, Y. Shimonishi and T. Takao, "Differentiating α-and β-aspartic acids by electrospray ionization and low-energy tandem mass spectrometry." Rapid Commun. Mass Spectrom. 14, 2092 (2000).
14. P. Roepstorff and J. Fohlman, "Proposal for a common nomenclature for sequence ions in mass spectra of peptides," Biomed. Mass Spectrom. 11, 601 (1984).
15. W. Yu, J.E. Vath, M.C. Huberty and S.A. Martin, "Identification of the facile gas-phase cleavage of the Asp-Pro and Asp-Xxx peptide bonds in matrix-assisted laser desorption time-of-flight mass spectrometry," Anal. Chem. 65, 3015 (1993).
16. R. Bakhtiar, Q. Wu, S.A. Hofstadler and R.D. Smith, "Charge state specific facile gas-phase cleavage of Asp 75-Met 76 peptide bond in the α-chain of human apohemoglobin probed by electrospray ionization mass spectrometry," Biol. Mass Spectrom. 23, 101 (1994).
17. J. Qin and B.T. Chait, "Preferential Fragmentation of Protonated Gas-Phase Peptide Ions Adjacent to Acidic Amino Acid Residues," J. Am. Chem. Soc. 117, 5411 (1995).
18. G. Tsaprailis, H. Nair, A. Somogyi, V.H. Wysocki, W. Zhong, J.H. Futrell, S.G. Sommerfield and S.J. Gaskell, "Influence of secondary structure on the fragmentation of protonated peptides," J. Am. Chem. Soc. 121, 5142 (1999).
19. C. Gu. A. Somogyi, V.H. Wysocki and K.F. Medzihradszky, "Fragmentation of protonated oligopeptides XLDVLQ (X=L, H, K or R) by surface induced dissociation: additional evidence for the 'mobile proton' model," Anal. Chim. Acta 397, 278 (1999).
20. G. Tsaprailis, A. Somogyi, E.N. Nikolaev and V.H. Wysocki, "Refining the model for selective cleavage at acidic residues in arginine-containing protonated peptides." Int. J. Mass Spectrom. 195/197, 467 (2000).
21. C. Gu, G. Tsaprailis, L. Breci and V.H. Wysocki, "Selective gas-phase cleavage at the peptide bond C-terminal to aspartic acid in fixed-charge derivatives of Asp-containing peptides." Anal. Chem. 72, 5804 (2000).
22. V.H. Wysocki, G. Tsaprailis, L.L. Smith and L.A. Breci, "Mobile and localized protons: a framework for understanding peptide dissociation." J. Mass Spectrom. 37, 1399 (2000).
23. T.H. Bailey, J. Laskin and J.H. Futrell, "Energetics of selective cleavage at acidic residues studies by time-and energy-resolved surface-induced dissociation in FT-ICR MS." Int. J. Mass Spectrom. 222, 313 (2003).
24. A.R. Dongre, J.L. Jones, A. Somogyi and V.H. Wysocki, "Influence of Peptide Composition, Gas-Phase Basicity, and Chemical Modification on Fragmentation Efficiency: Evidence for the Mobile Proton Model," J. Am. Chem. Soc. 118, 8365 (1996).
25. For a review of FT-MS apparatus and methods see A.G. Marshall, C.L. Hendrickson and G.S. Jackson, "Fourier Transform Ion Cyclotron Resonance Mass Spectrometry: A Primer." Mass Spectrom. Rev. 17, 1 (1998).