Disulfide bond mapping by cyanylation-induced cleavage and mass spectrometry

Methods in Molecular Biology

Volumn 446, Issue , 2008, Pages 1-20

  Wu, Jiang ^a  

^a PFIZER INC   (United States)

Author keywords

Chemical cleavage; Cyanylation; Disulfi de; Mass mapping

Indexed keywords

EID: 84934435651     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-60327-84-7_1     Document Type: Article

References (24)

1. Creighton, T. E. (1984) Disulfide bond formation in proteins, in Methods in Enzymol, 107, (Wold, F. and Moldave, K. eds.), Academic, San Diego, CA, pp.305-329.
2. Gorman, J. J., Wallis, T. P., and Pitt, J. J. (2002) Protein disulfide bond determination by mass spectrometry. Mass Spectrom. Rev. 21, 183-216.
3. Smith, D. L. and Zhou, Z. (1990) Strategies for locating disulfide bonds in proteins, in Methods in Bnzymology, vol. 193, (McCloskey, J. A. ed.), Academic, NY, pp.374-389.
4. Hirayama, K. and Akashi, S. (1994) Assignment of disulfide bonds in proteins, in Biological Mass Spectrometry: Present and Future (Matsuo, T., Caprioli, R. M., Gross, M. L., and Seyama, Y., eds), Wiley, NY, pp.299-312.
5. Jacobson, G. R., Schaffer, M. H., Stark, G. R., and Vanaman, T. C. (1973) Specific chemical cleavage in high yield at the amino peptide bonds of cysteine and cystine residues. J. Biol. Chem. 248, 6583-6591.
6. Wakselman, M., Guibe-Jampel, E. (1976) 1-Cyano-4-dimethylamino-pyridinium salts: new water-soluble reagents for the cyanylation of protein sulphydryl groups. J. C. S. Chem. Comm. 21-22.
7. Nakagawa, S., Tamakashi, Y., Hamaná, T., Kawase, M., Taketomi, S., Ishibashi, Y., Nishimura, O., Fukuda, T. (1994) Chemical cleavage of recombinant fusion proteins to yield peptide amides. J. Am. Chem. Soc. 116, 5513-5514.
8. Nakagawa, S., Tamakashi, Y., Ishibashi, Y., Kawase, M., Taketomi, S., Nishimura, O., Fukuda, T. (1994) Production of human PTH (1-34) via a recombinant DNA technique. Biochem. Biophys. Res. Commun. 200, 1735-1741.
9. Wu, J., Watson, J. T. (1998) Optimization of the cleavage reaction for cyanylated cysteinyl proteins for efficient and simplified mass mapping. Anal. Biochem. 258, 268-276.
10. Pipes, G. D., Kosky, A. A., Abel, J., Zhang, Y., Treuheit, M. J., Kleemann, G. R. (2005) Optimization and application of CDAP labeling for the assignment of cysteines. Pharma. Res. 22, 1059-1068.
11. Gallegos-Perez, J. L., Rangel-Ordonez, L., Bowman, S. R., Ngowe, C. O., Watson, J. T. (2005) Study of primary amines for nucleophilic cleavage of cyanylated cystinyl proteins in disulfide mass mapping methodology. Anal. Biochem. 346, 311-319.
12. Wu, J., Gage, D. A., Watson, J. T. (1996) A strategy to locate cysteine residues in proteins by specific chemical cleavage followed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal Biochem 235, 161-174.
13. Wu, J., Watson, J. T. (1997) A novel methodology for assignment of disulfide bond pairings in proteins. Protein Sci 6, 391-398.
14. Yang, Y., Wu, J. Watson, J. T. (1998) Disulfide mass mapping in proteins containing adjacent cysteines is possible with cyanylation/cleavage methodology. J. Am. Chem. Soc. 120, 5834-5835.
15. Qi, J., Wu, J., Somkuti, G. A., Watson, J. T. (2001) Determination of the disulfide structure of sillucin, a highly knotted, cysteine-rich peptide, by cyanylation/cleavage mass mapping. Biochemistry. 40, 4531-4538.
16. Borges, C. R., Qi, J., Wu, W., Torng, E., Hinck, A. P., Watson JT. (2004) Algorithm-assisted elucidation of disulfide structure: application of the negative signature mass algorithm to mass-mapping the disulfide structure of the 12-cysteine transforming growth factor beta type II receptor extracellular domain. Anal Biochem. 329, 91-103.
17. Putney, S., Herlihy, W., Royal, N., Pang, H., Aposhian, H. V., Pickering, L., Belagaje, R., Biemann, K., Page, D., Kuby, S., Schimmel, P. (1984) Rabbit muscle creatine Phosphokinase cDNA clone, primary structure and detection of human homologues. J. Biol. Chem., 259, 14317-14320.
18. Schutte, C. G., Lemm, T., Glombitza, G. J., Sandhoff, K (1998) Complete localization of disulfide bonds in GM2 activator protein. Protein Sei. 7, 1039-1045.
19. Wu, J., Yang, Y., Watson, J. T. (1998) Trapping of intermediates during the refolding of recombinant human epidermal growth factor (hEGF) by cyanylation, and subsequent structural elucidation by mass spectrometry. Protein Sci. 7, 1017-1028.
20. Somkuti, G. A., Walter, M. M. (1970) Antimicrobial polypeptide synthesized by Mucor pusillus NRRL 2543. Proc Soc Exp Biol Med. 133, 780-785.
21. Gray, W. R. (1993). Disulfide structures of highly bridged peptides: A new strategy for analysis. Protein Sci. 2, 1732-1748.
22. Gray, W. R. (1993) Echistatin disulfide bridges: selective reduction and linkage assignment. Protein Sci. 2, 1749-1755.
23. Qi, J., Wu, W., Borges, C. R., Hang, D., Rupp, M., Torng, E., Watson, J. T. (2003) Automated data interpretation based on the concept of "negative signature mass" for mass-mapping disulfide structures of cystinyl proteins. J. Am. Soc. Mass Spectrom. 14, 1032-1038).
24. Rubinstein, M. (1979) Preparative high-performance liquid partition chromatography of proteins. Anal. Biochem. 98, 1-7.