Synthesis and evaluation of bioorthogonal pantetheine analogues for in vivo protein modification

Journal of the American Chemical Society

Volumn 128, Issue 37, 2006, Pages 12174-12184

  Meier, Jordan L ^a   Mercer, Andrew C ^a   Rivera Jr , Heriberto ^a   Burkart, Michael D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CELLS; CHEMICAL BONDS; FUSION REACTIONS; MOLECULAR STRUCTURE; REACTION KINETICS;

CRUDE CELL LYSATE; FUSION SYSTEMS; PROTEIN LABELING; PROTEIN TAGGING; PROTEOMICS;

PROTEINS;

AMIDE; CARRIER PROTEIN; NATURAL PRODUCT; PANTETHEINE; PANTETHEINE DERIVATIVE; PANTOTHENAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBODY DETECTION; ARTICLE; BINDING SITE; CELL LYSATE; EVALUATION; IN VIVO STUDY; PROTEIN BINDING; PROTEIN MODIFICATION; PROTEOMICS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BACTERIAL PROTEINS; CARRIER PROTEINS; COENZYME A; ESCHERICHIA COLI; KINETICS; PANTETHEINE; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TRANSFERASES (OTHER SUBSTITUTED PHOSPHATE GROUPS);

EID: 33748776033     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063217n     Document Type: Article

References (46)

1. Bertozzi, C. R.; Prescher, J. A. Nat. Chem. Biol. 2005, 1, 13-21.
2. (a) Tsien, R. Y. Annu. Rev. Biochem. 1998, 67, 509-544.
3. (b) Lippincott-Schwartz, J.; Patterson, G. H. Science 2003, 300, 87-91.
4. (a) Fritze, C. E.; Anderson, T. R. Methods Enzymol. 2000, 327, 3-16.
5. (b) Massoud, T. F.; Gambhir, S. S. Genes Dev. 2003, 17, 545-580.
6. Clarke, K. M.; Mercer, A. C.; La Clair, J. J.; Burkart, M. D. J. Am. Chem. Soc. 2005, 127, 11234-11235.
7. (a) La Clair, J. J.; Foley, T. L.; Schegg, T. R.; Regan, C. M.; Burkart, M. D. Chem. Biol. 2004, 11, 195-201.
8. (b) Yin, J.; Liu, F.; Li, X.; Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 7754-7755.
9. (c) Yin, J.; Liu, F.; Schinke, M.; Daly, C.; Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 13570-13571.
10. (a) George, N.; Pick, H.; Vogel, H.; Johnsson, N.; Johnsson, K. J. Am. Chem. Soc. 2004, 126, 8896-8897.
11. (b) Yin, J.; Lin, A. J.; Buckett, P. D.; Wessling-Resnick, M.; Golan, D. E.; Walsh, C. T. Chem. Biol. 2005, 12, 999-1006.
12. (c) Vivero-Pol L.; George, N.; Krumm, H.; Johnsson, K.; Johnsson, N. J. Am. Chem. Soc. 2005, 127, 12770-12771.
13. Yin, J.; Straight, P. D.; McLoughlin, S. M.; Zhou, Z.; Lin, A. J.; Golan, D. E.; Kelleher, N. L.; Kolter, R.; Walsh, C. T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 15815-15820.
14. (a) Mahal, L. K.; Yarema, K. J.; Bertozzi, C. R. Science 1997, 276, 1125-1128.
15. (b) Yarema, K. J.; Mahal, L. K.; Bruehl, R.; Rodriguez, E. C.; Bertozzi, C. R. J. Biol. Chem. 1998, 273, 31168-31179.
16. (c) Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007-2010.
17. (a) Speers, A. E.; Gravait, B. F. Chem. Biol. 2004, 11, 535-546.
18. (b) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687.
19. (c) Alexander, J. P.; Cravatt, B. F. Chem Biol. 2005, 12, 1179-1187.
20. (a) Hwan-Ching, T.; Khidekel, N.; Ficarro, S. B.; Peters, E. C.; Hsieh-Wilson, L. C. J. Am. Chem. Soc. 2004, 126, 10500-10501.
21. (b) Khidekel, N.; Ficarro, S. B.; Peters, E. C.; Hsieh-Wilson, L. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 36, 13132-13137.
22. Mandel, A. L.; La Clair, J. J.; Burkart, M. D. Org. Lett. 2004, 6, 4801-4803.
23. Virga, K. G.; Zhang, Y. M.; Leonardi, R.; Ivey, R. A.; Hevener, K.; Park, H. W.; Jackowski, S.; Rock, C. O.; Lee, R. E. Bioorg. Med. Chem. 2006, 14, 1007-1020.
24. Jackowski, S.; Rock, C. O. J. Bacteriol. 1981, 148, 926-932.
25. Worthington, A. S.; Burkart, M. D. Org. Biomol. Chem. 2005, 4, 44-46.
26. Kumar, V.; Aldrich, J. V. Org. Lett. 2003, 5, 613-616.
27. Dueno, E. E.; Chu, F.; Kim, S. I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843-1846.
28. (a) Michelson, A. M. Biochim. Biophys. Acta 1964, 93, 71-77.
29. (b) Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1961, 83, 663-675.
30. Krause, B. R. et al. Synth. Commun. 2006, 36, 365-391.
31. 3, reflux) was used.
32. La Clair, J. J.; et al. ChemBioChem 2006, 7, 409-416.
33. Strauss, E.; Begley, T. P. J. Biol. Chem. 2002, 277, 48205-48209.
34. Mercer, A. C.; La Clair, J. J.; Burkart, M. D. ChemBioChem 2005, 8, 1335-1337.
35. Ivey, R. A.; Zhang, Y.; Virga, K. G.; Hevener, K.; Lee, R. E.; Rock, C. O.; Jackowski, S.; Park, H. J. Biol. Chem. 2004, 279, 35622-35629.
36. This comparison refers to kinetic data compiled for alternatively linked dansyl and DMACA-pantetheine analogues in ref 14.
37. Rock, C. O.; Calder, R. B.; Karim, M. A.; Jackowski, S. J. Biol. Chem. 2000, 275, 1377-1383.
38. Jackowski, S.; Alix, J. H. J. Bacteriol. 1990, 172, 3842-3848.
39. Kohn M, Breinbauer R. Angew. Chem., Int. Ed. 2004, 43, 3106-3116.
40. (a) Simon Jenni, S.; Leibundgut, M.; Maier, T.; Ban, N. Science 2006, 311, 1258-1262.
41. (b) Maier, T.; Jenni, S.; Ban, N. Science 2006, 311, 1263-1267.
42. Leonardi, R.; Chohnan, S.; Zhang, Y.; Virga, K. G.; Lee, R. E.; Rock, C. O.; Jackowski, S. J. Biol. Chem. 2005, 280, 3314-3322.
43. Choudhry, A. E.; Mandichak, T. L.; Broskey, J. P.; Egolf, R. W.; Kinsland, C.; Begley, T. P.; Seefeld, M. A.; Ku, T. W.; Brown, J. R.; Zalacain, M.; Ratnam, K. Antimicrob. Agents Chemother. 2003, 47, 2051-2055.
44. Brand, L. A.; Strauss, E. J. Biol. Chem. 2005, 280, 20185-20188.
45. Chen, I.; Ting, A. Y. Curr. Opin. Biotechnol. 2005, 16, 35-40.
46. Abbreviations: CoA, Coenzyme A; PPTase, phosphopantetheinyltransferase; O-GlcNAc, O-linked β-N-acetylglucosamine; β-Ala, β-alanine; PANK, pantothenate kinase; CoaA, ecoli PANK; CoaD, E. coli phosphopantetheine adenylytransferase; CoaE, E. coli dephospho-CoA kinase PEG, poly(ethylene glycol); Pantolactone, (D)-(-)-pantolactone; Boc, tert-butyl carbamate; Alloc, allyl-carbamate; DMACA, 7-dimethylaminocoumarin-4-acetic acid; CP, carrier protein; ACP, fatty acid synthase acyl carrier protein from E. coli; VibB, vibriobactin synthase carrier protein from Vibrio cholerae; Fren. frenolicin synthase carrier protein from Streptomyces roseofulvus; panF, pantothenate permease.