CE-MS identification of amino acid sequence inversion as a new degradation pathway of an aspartyl model tripeptide

Chromatographia

Volumn 75, Issue 19-20, 2012, Pages 1205-1210

  Brückner, Christin ^a   Bunz, Svenja Catharina ^b   Neusü, Christian ^b   Scriba, Gerhard K E ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b AALEN UNIVERSITY   (Germany)

Author keywords

Aspartyl peptide; Capillary electrophoresis; Mass spectrometry; Sequence inversion

Indexed keywords

ASPARTIC ACID; GLYCINE; PHENYLALANINE; PHENYLALANYLALPHAASPARTYLGLYCINE TRIPEPTIDE; TRIPEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; AQUEOUS SOLUTION; ARTICLE; CAPILLARY ELECTROCHROMATOGRAPHY; CYCLIZATION; DIASTEREOISOMER; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; ISOMERIZATION; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN HYDROLYSIS; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SIGNAL TRANSDUCTION;

EID: 84867012600     PISSN: 00095893     EISSN: 16121112     Source Type: Journal    
DOI: 10.1007/s10337-012-2306-5     Document Type: Article

References (24)

1. Manning MC, Chou DK, Murphy BM, Payne RW, Katayama DS (2010) Stability of protein pharmaceuticals: an update. Pharm Res 27(4):544-575. doi:10.1007/s11095-009-0045-6
2. Manning MC, Patel K, Borchardt RT (1989) Stability of protein pharmaceuticals. Pharm Res 6(11):903-918
3. Aswad DW (1995) Deamidation and isoaspartate formation in peptides and proteins. CRC series in analytical biotechnology. CRC Press, Boca Raton
4. Geiger T, Clarke S (1987) Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides. Succinimide-linked reactions that contribute to protein degradation. J Biol Chem 262(2):785-794
5. Stephenson RC, Clarke S (1989) Succinimide formation from aspartyl and asparaginyl peptides as a model for the spontaneous degradation of proteins. J Biol Chem 264(11):6164-6170
6. Oliyai C, Borchardt RT (1994) Chemical pathways of peptide degradation. VI. Effect of the primary sequence on the pathways of degradation of aspartyl residues in model hexapeptides. Pharm Res 11(5):751-758
7. Radkiewicz JL, Zipse H, Clarke S, Houk KN (1996) Accelerated racemization of aspartic acid and asparagine residues via succinimide intermediates: an ab initio theoretical exploration of mechanism. J Am Chem Soc 118(38):9148-9155
8. Oliyai C, Patel JP, Carr L, Borchardt RT (1994) Chemical pathways of peptide degradation.VII. Solid-state chemical-instability of an aspartyl residue in a model hexapeptides. Pharm Res 11(6):901-908
9. Bada JL (1984) In vivo racemization in mammalian proteins. Methods Enzymol 106:98-115
10. Ritz-Timme S, Collins MJ (2002) Racemization of aspartic acid in human proteins. Ageing Res Rev 1(1):43-59
11. Hekman CM, DeMond WS, Kelley PJ, Mauch SF, Williams JD (1999) Isolation and identification of cyclic imide and deamidation products in heat stressed pramlintide injection drug product. J Pharm Biomed Anal 20(5):763-772
12. Won CM, Molnar TE, Windisch VL, McKean RE (1999) Kinetics and mechanism of degradation of klerval, a pseudotetrapeptide. Int J Pharm 190(1):1-11
13. Fisher GH, Payan IL, Chou SJ, Man EH, Cerwinski S, Martin T, Emory C, Frey WH 2nd (1992) Racemized D-aspartate in Alzheimer neurofibrillary tangles. Brain Res Bull 28(1):127-131
14. Orpiszewski J, Schormann N, Kluve-Beckerman B, Liepnieks JJ, Benson MD (2000) Protein aging hypothesis of Alzheimer disease. FASEB J 14(9):1255-1263
15. Fischer PM (2003) Diketopiperazines in peptide and combinatorial chemistry. J Pept Sci 9(1):9-35. doi:10.1002/psc.446
16. Conrad U, Taichrib A, Neusu C, Scriba GKE (2010) Capillary electrophoresis analysis of the degradation of the aspartyl tripeptide Phe-Asp-GlyOH at pH 2.0 and 7.4 under forced conditions. J Pharm Biomed Anal 51(3):640-648. doi:10.1016/j.jpba. 2009.09.044
17. DeHart MP, Anderson BD (2007) The role of the cyclic imide in alternate degradation pathways for asparagine-containing peptides and proteins. J Pharm Sci 96(10):2667-2685. doi:10.1002/Jps.20905
18. Chan WC, White PD (2000) Fmoc Solid Phase Peptide Synthesis. Oxford Press, Oxford
19. Carpino LA (1993) 1-Hydroxy-7-azabenzotriazole-an efficient peptide coupling additive. J Am Chem Soc 115(10):4397-4398
20. Biemann K (1990) Appendix 5. Nomenclature for peptide fragment ions (positive ions). Methods Enzymol 193:886-887
21. Roepstorff P, Fohlman J (1984) Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed Mass Spectrom 11(11):601. doi:10.1002/bms.1200111109
22. De Boni S, Neusu C, Pelzing M, Scriba GKE (2003) Identification of degradation products of aspartyl tripeptides by capillary electrophoresis-tandem mass spectrometry. Electrophoresis 24(5):874-882. doi:10.1002/elps.200390110
23. Lehmann WD, Schlosser A, Erben G, Pipkorn R, Bossemeyer D, Kinzel V (2000) Analysis of isoaspartate in peptides by electrospray tandem mass spectrometry. Protein Sci 9(11):2260-2268. doi:10.1110/ps.9.11.2260
24. Sepetov NF, Krymsky MA, Ovchinnikov MV, Bespalova ZD, Isakova OL, Soucek M, Lebl M (1991) Rearrangement, racemization and decomposition of peptides in aqueous solution. Pept Res 4(5):308-313