Chemical methods for the detection of protein N-homocysteinylation via selective reactions with aldehydes

Analytical Chemistry

Volumn 81, Issue 21, 2009, Pages 9065-9071

  Zang, Tianzhu ^a   Dai, Shujia ^a   Chen, Dajun ^a   Lee, Bobby W K ^a   Liu, Suli ^a   Karger, Barry L ^a   Zhou, Zhaohui Sunny ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; AMINE GROUPS; AMINO GROUP; AMINOTHIOLS; BIOLOGICAL SAMPLES; BLOOD LEVELS; CHEMICAL METHOD; GEL ELECTROPHORESIS; HOMOCYSTEINES; HYPERHOMOCYSTEINEMIA; LYSINE RESIDUES; NATIVE PROTEINS; POST-TRANSLATIONAL MODIFICATIONS; SAMPLE COMPLEXITY; SCHIFF BASE FORMATION; SELECTIVE REACTIONS;

AMIDES; AMINATION; AMINES; AMINO ACIDS; CHEMICAL REACTIVITY; ELECTROPHORESIS; FUNCTIONAL GROUPS; HEMOGLOBIN; RESINS; THERMOLUMINESCENCE;

ALDEHYDES;

1,3 THIAZINE DERIVATIVE; ALDEHYDE; ALDEHYDE DERIVATIVE; AMINE; AMINOTHIOL; BIOTIN; FLUORESCENT DYE; HEMOGLOBIN; HOMOCYSTEINE; HOMOCYSTEINE THIOLACTONE; LYSINE; RESIN; SCHIFF BASE;

ARTICLE; BLOOD LEVEL; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYTOTOXICITY; GEL ELECTROPHORESIS; HOMOCYSTINURIA; HUMAN; HYPERHOMOCYSTEINEMIA; METABOLITE; MOUSE; NONHUMAN; PLASMA; PROTEIN ANALYSIS; PROTEIN PROCESSING; PROTEIN STRUCTURE; PROTON TRANSPORT; RAT; STOICHIOMETRY;

ALDEHYDES; AMINO ACID SEQUENCE; ANIMALS; BLOTTING, WESTERN; CHEMILUMINESCENT MEASUREMENTS; FLUORESCENT DYES; HEMOGLOBINS; HOMOCYSTEINE; HUMANS; MASS SPECTROMETRY; MICE; RATS; RHODAMINES;

EID: 70350645116     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac9017132     Document Type: Article

References (37)

1. Maron, B. A.; Loscalzo, J. Annu. Rev. Med. 2009, 60, 39-54.
2. Joseph, J.; Joseph, L. Metab. Syndr. Relat. Disord. 2003, 1, 97-104.
3. Carmel, R.; Jacobsen, D. W. Homocysteine in health and disease; Cambridge University Press: Cambridge, U.K., 2001.
4. Selhub, J.; Jacques, P. F.; Wilson, P. W.; Rush, D.; Rosenberg, I. H. J. Am. Med. Assoc. 1993, 270, 2693-2698.
5. Mudd, S. H.; Finkelstein, J. D.; Irreverre, F.; Laster, L. Science 1964, 143, 1443-1445.
6. Finkelstein, J. D. Semin. Thromb. Hemostasis 2000, 26, 219-225.
7. Goyette, P.; Sumner, J. S.; Milos, R.; Duncan, A. M.; Rosenblatt, D. S.; Matthews, R. G.; Rozen, R. Nat. Genet. 1994, 7, 195-200.
8. De Wals, P.; Tairou, F.; Van Allen, M. I.; Uh, S. H.; Lowry, R. B.; Sibbald, B.; Evans, J. A.; Van den Hof, M. C.; Zimmer, P.; Crowley, M.; Fernandez, B.; Lee, N. S.; Niyonsenga, T. N. Engl. J. Med. 2007, 357, 135-142.
9. Jacobsen, D. W. Clin. Chem. 2009, 55, 1742-1743.
10. Jakubowski, H. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 4504-4508.
11. Jakubowski, H. J. Physiol. Pharmacol. 2008, 59 (Suppl. 9), 155-167.
12. Jakubowski, H. FASEB J. 1999, 13, 2277-2283.
13. Jakubowski, H. J. Biol. Chem. 1997, 272, 1935-1942.
14. Undas, A.; Perla, J.; Lacinski, M.; Trzeciak, W.; Kazmierski, R.; Jakubowski, H. Stroke 2004, 35, 1299-1304.
15. Glowacki, R.; Jakubowski, H. J. Biol. Chem. 2004, 279, 10864-10871.
16. Jakubowski, H. Anal. Biochem. 2008, 380, 257-261.
17. Perla-Kajan, J.; Marczak, L.; Kajan, L.; Skowronek, P.; Twardowski, T.; Jakubowski, H. Biochemistry 2007, 46, 6225-6231.
18. Sauls, D. L.; Lockhart, E.; Warren, M. E.; Lenkowski, A.; Wilhelm, S. E.; Hoffman, M. Biochemistry 2006, 45, 2480-2487.
19. Perla-Kajan, J.; Stanger, O.; Luczak, M.; Ziolkowska, A.; Malendowicz, L. K.; Twardowski, T.; Lhotak, S.; Austin, R. C.; Jakubowski, H. Biomed. Pharmacother. 2008, 62, 473-479.
20. Wang, D.; Crowe, W. E.; Strongin, R. M.; Sibrian-Vazquez, M. Chem. Commun. (Cambridge, U.K.) 2009, 1876-1878.
21. Wang, W.; Escobedo, J. O.; Lawrence, C. M.; Strongin, R. M. J. Am. Chem. Soc. 2004, 126, 3400-3401.
22. Strongin, R., Portland State University, personal communication, 2009.
23. Jakubowski, H. Chemistry 2006, 12, 8039-8043.
24. Rusin, O.; St Luce, N. N.; Agbaria, R. A.; Escobedo, J. O.; Jiang, S.; Warner, I. M.; Dawan, F. B.; Lian, K.; Strongin, R. M. J. Am. Chem. Soc. 2004, 126, 438-439.
25. Wang, W.; Rusin, O.; Xu, X.; Kim, K. K.; Escobedo, J. O.; Fakayode, S. O.; Fletcher, K. A.; Lowry, M.; Schowalter, C. M.; Lawrence, C. M.; Fronczek, F. R.; Warner, I. M.; Strongin, R. M. J. Am. Chem. Soc. 2005, 127, 15949-15958.
26. Zhang, D.; Zhang, M.; Liu, Z.; Yu, M.; Li, F.; Yi, T.; Huang, C. Tetrahedron Lett. 2006, 47, 7093-7096.
27. Hilgers, M. T.; Ludwig, M. L. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 11169-11174.
28. Alfaro, J. F.; Gillies, L. A.; Sun, H. G.; Dai, S.; Zang, T.; Klaene, J. J.; Kim, B. J.; Lowenson, J. D.; Clarke, S. G.; Karger, B. L.; Zhou, Z. S. Anal. Chem. 2008, 80, 3882-3889.
29. Fülöp, F.; Mattinen, J.; Pihlaja, K. Tetrahedron 1990, 46, 6545-6552.
30. Giron, P.; Dayon, L.; David, F.; Sanchez, J. C.; Rose, K. J. Proteomics 2009, 71, 647-661.
31. Tam, J. P.; Miao, Z. J. Am. Chem. Soc. 1999, 121, 9013-9022.
32. Rejtar, T., Northeastern University, personal communication, 2009.
33. Choudhary, C.; Kumar, C.; Gnad, F.; Nielsen, M. L.; Rehman, M.; Walther, T.; Olsen, J. V.; Mann, M. Science 2009 (in press).
34. Schroeder, M. J.; Shabanowitz, J.; Schwartz, J. C.; Hunt, D. F.; Coon, J. J. Anal. Chem. 2004, 76, 3590-3598.
35. Villen, J.; Beausoleil, S. A.; Gygi, S. P. Proteomics 2008, 8, 4444-4452.
36. Zhang, Q.; Petyuk, V. A.; Schepmoes, A. A.; Orton, D. J.; Monroe, M. E.; Yang, F.; Smith, R. D.; Metz, T. O. Rapid Commun. Mass Spectrom. 2008, 22, 3027-3034.
37. Zumwalt, A.; Choudhary, G.; Cho, D.; Hemenway, E.; Mylchreest, I. Proceedings of the 51st ASMS Confererence on Mass Spectrometry and Allied Topics, 2003.