Letter: β-Cyclodextrin affects the formation of isomerization products during peptide deamidation

European Journal of Mass Spectrometry

Volumn 21, Issue 4, 2015, Pages 701-705

  Qi, Yulin ^a   Volmer, Dietrich A ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Amyloid b; Cyclodextrin; Deamidation; ECD; FTICR MS; Isomerization

Indexed keywords

AMINO ACIDS; CYCLODEXTRINS; ELECTROSPRAY IONIZATION; GLYCOPROTEINS; ISOMERIZATION; ISOMERS; MASS SPECTROMETRY; NEURODEGENERATIVE DISEASES;

ALZHEIMER'S DISEASE; AMYLOID PLAQUES; BETA-CYCLODEXTRIN; DEAMIDATION; ELECTRON CAPTURE DISSOCIATION; FOURIER TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETRY; FT-ICR MS; PROTEIN AGGREGATION;

PEPTIDES;

AMYLOID; AMYLOID BETA PROTEIN; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE;

AMINO ACID SEQUENCE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ISOMERISM; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; AMYLOID; AMYLOID BETA-PEPTIDES; BETA-CYCLODEXTRINS; ISOMERISM; MOLECULAR SEQUENCE DATA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84945902463     PISSN: 14690667     EISSN: 17516838     Source Type: Journal    
DOI: 10.1255/ejms.1385     Document Type: Article

References (28)

1. N.E. Robinson and A.B. Robinson, "Molecular clocks", Proc. Natl Acad. Sci. 98, 944 (2001). doi: Http://dx.doi.org/10.1073/pnas.98.3.944
2. S. Clarke, "Propensity for spontaneous succinimide formationfrom aspartyl and asparaginyl residues in cellular proteins", Int. J. Pept. Protein Res. 30, 808 (1987). doi: Http://dx.doi.org/10.1111/j.1399-3011.1987.tb03390.x
3. T. Geiger and S. Clarke, "Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides", J. Biol. Chem. 262, 785 (1987).
4. S. Ritz-Timme and M.J. Collins, "Racemization of asparticacid in human proteins", Ageing Res. Rev. 1, 43 (2002). doi: Http://dx.doi.org/10.1016/S0047-6374(01)00363-3
5. P. Perez-Hurtado and P.B. O'Connor, "Deamidation of collagen", Anal. Chem. 84, 3017 (2012). doi: Http://dx.doi.org/10.1021/ac202980z
6. T. Shimizu, A. Watanabe, M. Ogawara, H. Mori and T. Shirasawa, "Isoaspartate formation and neurodegeneration in Alzheimer's disease", Arch. Biochem. Biophys. 381, 225 (2000). doi: Http://dx.doi.org/10.1006/abbi.2000.1955
7. A.E. Roher, J.D. Lowenson, S. Clarke, C. Wolkow, R. Wang, R.J. Cotter, I.M. Reardon, H.A. Zürcher-Neely, R.L. Heinrikson and M.J. Ball, "Structural alterations in the peptide backbone of beta-amyloid core protein may account for its deposition and stability in Alzheimer's disease", J. Biol. Chem. 268, 3072 (1993).
8. Y. Wakutani, K. Watanabe, Y. Adachi, K. Wada-Isoe, K. Urakami, H. Ninomiya, T.C. Saido, T. Hashimoto, T. Iwatsubo and K. Nakashima, "Novel amyloid precursorprotein gene missense mutation (D678n) in probable familial Alzheimer's disease", J. Neurol. Neurosurg. Psychiatry 75, 1039 (2004). doi: Http://dx.doi.org/10.1136/jnnp.2003.010611
9. T. Shimizu, Y. Matsuoka and T. Shirasawa, "Biological significance of isoaspartate and its repair system", Biol. Pharm. Bull. 28, 1590 (2005). doi: Http://dx.doi.org/10.1248/bpb.28.1590
10. M. Necula, R. Kayed, S. Milton and C.G. Glabe, "Small molecule inhibitors of aggregation indicate that amyloidb oligomerization and fibrillization pathways are independentand distinct", J. Biol. Chem. 282, 10311 (2007). doi: Http://dx.doi.org/10.1074/jbc.M608207200
11. P. Camilleri, N.J. Haskins and D.R. Hewlett, "b-Cyclodextrin interacts with the Alzheimer amyloid b-A4 peptide", FEBS Lett. 341, 256 (1994). doi: Http://dx.doi.org/10.1016/0014-5793(94)80467-2
12. P. Camilleri, N.J. Haskins, A.P. New and M.R. Saunders, "Analysing the complexation of amino acids and peptides with b-cyclodextrin using electrospray ionization mass spectrometry", Rapid Commun. Mass Spectrom. 7, 949 (1993). doi: Http://dx.doi.org/10.1002/rcm.1290071017
13. J. Waite, G.M. Cole, S.A. Frautschy, D.J. Connor and L.J. Thal, "Solvent effects on beta protein toxicity in vivo", Neurobiol. Aging 13, 595 (1992). doi: Http://dx.doi.org/10.1016/0197-4580(92)90062-3
14. A. Wahlström, R. Cukalevski, J. Danielsson, J. Jarvet, H. Onagi, J. Rebek, S. Linse and A. Gräslund, "Specific binding of a b-cyclodextrin dimer to the amyloid b peptide modulates the peptide aggregation process", Biochemistry (Mosc.) 51, 4280 (2012). doi: Http://dx.doi.org/10.1021/bi300341j
15. T. Loftsson and D. Duchêne, "Cyclodextrins and their pharmaceutical applications", Int. J. Pharm. 329, 1 (2007). doi: Http://dx.doi.org/10.1016/j.ijpharm.2006.10.044
16. S.V. Kurkov and T. Loftsson, "Cyclodextrins", Int. J. Pharm. 453, 167 (2013). doi: Http://dx.doi.org/10.1016/j.ijpharm.2012.06.055
17. K.N. Koushik, N. Bandi and U.B. Kompella, "Interaction of [d-Trp6, Des-Gly10] LHRH ethylamide and hydroxy propyl b-cyclodextrin (HPbCD): Thermodynamics of interaction and protection from degradation by a-chymotrypsin", Pharm. Dev. Technol. 6, 595 (2001). doi: Http://dx.doi.org/10.1081/PDT-120000297
18. J. Cunniff and P. Vouros, "False positives and the detection of cyclodextrin inclusion complexes by electrospray mass spectrometry", J. Am. Soc. Mass Spectrom. 6, 437 (1995). doi: Http://dx.doi.org/10.1016/1044-0305(95)00053-G
19. J. Ramirez, S. Ahn, G. Grigorean and C.B. Lebrilla, "Evidence for the formation of gas-phase inclusion complexes with cyclodextrins and amino acids", J. Am. Chem. Soc. 122, 6884 (2000). doi: Http://dx.doi.org/10.1021/ja000717m
20. Y. Qi, T. Geib and D. Volmer, "Determining the binding sites of b-cyclodextrin and peptides by electron-capture dissociation high resolution tandem mass spectrometry", J. Am. Soc. Mass Spectrom. 26, 1143 (2015). doi: Http://dx.doi.org/10.1007/s13361-015-1118-x
21. Y. Qi and P.B. O'Connor, "Data processing in Fourier transform ion cyclotron resonance mass spectrometry", Mass Spectrom. Rev. 33, 333 (2014). doi: Http://dx.doi.org/10.1002/mas.21414
22. P. Caravatti and M. Allemann, "The 'infinity cell': A new trapped-ion cell with radiofrequency covered trapping electrodes for Fourier transform ion cyclotron resonance mass spectrometry", Org. Mass Spectrom. 26, 514 (1991). doi: Http://dx.doi.org/10.1002/oms.1210260527
23. L.J. González, T. Shimizu, Y. Satomi, L. Betancourt, V. Besada, G. Padrón, R. Orlando, T. Shirasawa, Y. Shimonishi and T. Takao, "Differentiating a-and b-aspartic acids by electrospray ionization and low-energy tandem mass spectrometry", Rapid Commun. Mass Spectrom. 14, 2092 (2000). doi: Http://dx.doi.org/10.1002/1097-0231(20001130)14:223.0.CO;2-V
24. N.P. Sargaeva, C. Lin and P.B. O'Connor, "Identification of aspartic and isoaspartic acid residues in amyloidb peptides, including ab1-42, using electron-ion reactions", Anal. Chem. 81, 9778 (2009). doi: Http://dx.doi.org/10.1021/ac901677t
25. J.J. Cournoyer, C. Lin, L. Waskell and P.B. O'Connor, "Detecting isoaspartyl residues in proteins by electron capture dissociation", 53rd American Society for Mass Spectrometry Conference (San Antonio, Texas, 2005).
26. N. Leymarie, C.E. Costello and P.B. O'Connor, "electron capture dissociation initiates a free radical reaction cascade", J. Am. Chem. Soc. 125, 8949 (2003). doi: Http://dx.doi.org/10.1021/ja028831n
27. J.J. Cournoyer, C. Lin and P.B. O'Connor, "Detecting deamidation products in proteins by electron capture dissociation", Anal. Chem. 78, 1264 (2005). doi: Http://dx.doi.org/10.1021/ac051691q
28. U. Conrad, A. Fahr and G.K.E. Scriba, "Kinetics of aspartic acid isomerization and enantiomerization in model aspartyl tripeptides under forced conditions", J. Pharm. Sci. 99, 4162 (2010). doi: Http://dx.doi.org/10.1002/jps.22134