Peptide-cleaving catalyst selective for peptide deformylase

Journal of the American Chemical Society

Volumn 127, Issue 8, 2005, Pages 2396-2397

  Chae, Pil Seok ^a   Kim, Myoung Soon ^a   Jeung, Chul Seung ^a   Lee, Seong Du ^a   Park, Hwangseo ^a   Lee, Sangyoub ^a   Suh, Junghun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPLEX; PEPTIDE; PEPTIDE DEFORMYLASE;

ARTICLE; CATALYST; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PROTEIN DEGRADATION; REACTION ANALYSIS; SYNTHESIS;

AMIDES; AMIDOHYDROLASES; CATALYSIS; COBALT; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; PROTEIN CONFORMATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 14744276243     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044043h     Document Type: Article

References (27)

1. (a) Jeon, J. W.; Son, S. J.; Yoo, C. E.; Hong, I. S.; Song, J. B.; Suh, J. Org. Lett. 2002, 4, 4155-4158.
2. (b) Suh, J. Acc. Chem. Res. 2003, 36, 562-570.
3. (c) Jeon, J. W.; Son, S. J.; Yoo, C. E.; Hong, I. S.; Suh, J. Bioorg. Med. Chem. 2003, 11, 2901-2910.
4. For general discussion of hydrolytic peptide cleavage by metal complexes either tethered or untethered to the substrates, see: (a) Sutton, P. A.; Buckingham, D. A. Acc. Chem. Res. 1987, 20, 357-364.
5. (b) Chin, J.; Jubian, V.; Mrejen, K. J. Chem. Soc., Chem. Commun. 1990, 1326-1328.
6. (c) Suh, J. Acc. Chem. Res. 1992, 25, 273-279.
7. (d) Zhu, L.; Qin, L.; Parac, T. N.; Kostic, N. M. J. Am. Chem. Soc. 1994, 116, 5218-5224.
8. (e) Hegg, E. L.; Burstyn, J. N. J. Am. Chem. Soc. 1995, 117, 7015-7016.
9. (f) Jane, B.-B.; Lee, K.-P.; Min, D.-H.; Suh, J. J. Am. Chem. Soc. 1998, 120, 12008-12016.
10. (g) Kasai, M.; Ravi, R. G.; Shealy, S. J.; Grant, K. B. Inorg. Chem. 2004, 43, 6130-6132.
11. For site-selective hydrolytic peptide cleavage by metal complexes untethered to the substrates, see: (a) Moon, S.-J.; Jeon, J. W.; Kim, H.; Suh, M. P.; Suh, J. J. Am. Chem. Soc. 2000, 122, 7742-7749.
12. (b) Suh, J.; Moon, S.-J. Inorg. Chem. 2001, 40, 4890-4895.
13. (c) Yoo, C. E.; Chae, P. S.; Kim, J. E.; Jeong, E. J.; Suh, J. J. Am. Chem. Soc. 2003, 125, 14580-14589.
14. (d) Milovic, N. M.; Badjic, J. D.; Kostic, N. M. J. Am. Chem. Soc. 2004, 126, 696-697.
15. For site-selective peptide cleavage by metal complexes in the presence of oxidoreductive additives, see: (a) Shepartz, A.; Cuenoud, B. J. Am. Chem. Soc. 1990, 112, 3247-3249.
16. (b) Hoyer, D.; Cho, H.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 3249-3250.
17. (c) Rana, T. M.; Meares, C. F. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10578-10582.
18. Ravi Rajagopalan, P. T.; Grimme, S.; Pei, D. Biochemistry 2000, 39, 779-790.
19. Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
20. Expected values are 71, 227, and 298 if the cleavage site is Ala(17)-Lys(18).
21. In the study on Mb-cleaving catalysts,1a,c kinetic data were collected by electrophoresis, which requires a much larger amount of the protein than the total amount (1.5 mg) of PDF used in this work. Kinetic analysis was, therefore, mainly performed with MALDI-TOF MS data in this study.
22. Hollemeyer, K.; Altmeyer, W.; Heinzle, E. Anal. Chem. 2002, 74, 5960-5968.
23. α atoms during the entire course of simulation, indicating that the movement of Co(III)1 on the protein surface is highly restricted compared to the conformational change of the protein. See Supporting Information for details of theoretical analysis.
24. Becker, A.; Schlichting, I.; Kabsch, W.; Groche, D.; Schultz, S.; Wagner, A. F. Nat. Struct. Biol. 1998, 5, 1053-1058.
25. Attempts to isolate (R)-1 or (S)-1 by resolution of 1 or enantioselective stepwise synthesis were unsuccessful.
26. When tested with 15 other proteins listed in the Supporting Information, Co(III)1 did not cleave the proteins.
27. Docking simulation of Co(III)1 in the active site of PDF indicated that the active site was too narrow to accommodate Co(III)1 properly, and thus, the binding in the active site causes bad van der Waals contacts between protein and catalyst atoms.