Investigating the role of the geminal dimethyl groups of coenzyme A: Synthesis and studies of a didemethyl analogue

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 10, 2000, Pages 2451-2460

  Vogel, Kurt W ^a   Stark, Lucy M ^a   Mishra, Pranab K ^b   Yang, Wei ^b   Drueckhammer, Dale G ^b  

^a STANFORD UNIVERSITY   (United States)

^b STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL COENZYME A; CARNITINE ACETYLTRANSFERASE; COENZYME A; INORGANIC PYROPHOSPHATASE;

ARTICLE; DRUG SYNTHESIS; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME STRUCTURE; ENZYME SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; REACTION ANALYSIS;

CARNITINE O-ACETYLTRANSFERASE; CHLORAMPHENICOL O-ACETYLTRANSFERASE; COENZYME A; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PROTEIN CONFORMATION;

EID: 0033816578     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00189-9     Document Type: Article

References (49)

1. Lee, C.-H.; Chen, A. F. In The Pyridine Nucleotide Coenzymes; Everse, J., Anderson, B., You, K., Eds.; Academic: New York, 1982; p 189.
2. Primerano, D.; Burns, R. O. J. Bacteriol. 1982, 150, 1202. La Rossa, R. A.; VanDyk, T. K. J. Gen. Microbiol. 1989, 135, 2209.
3. Primerano, D.; Burns, R. O. J. Bacteriol. 1982, 150, 1202. La Rossa, R. A.; VanDyk, T. K. J. Gen. Microbiol. 1989, 135, 2209.
4. Fierke, C. A.; Jencks, W. P. J. Biol. Chem. 1986, 261, 7603. Whitty, A.; Fierke, C. A.; Jencks, W. P. Biochemistry 1995, 34, 11678.
5. Fierke, C. A.; Jencks, W. P. J. Biol. Chem. 1986, 261, 7603. Whitty, A.; Fierke, C. A.; Jencks, W. P. Biochemistry 1995, 34, 11678.
6. Lee C.-H., Sarma R.H. J. Am. Chem. Soc. 97:1975;1225.
7. Keire D.A., Robert J.M., Rabenstein D.L. J. Org. Chem. 57:1992;4427.
8. D'Ordine R.L., Paneth P., Anderson V.E. Bioorg. Chem. 23:1995;169.
9. Wu W.-J., Tonge P.J., Raleigh D.P. J. Am. Chem. Soc. 120:1998;9988.
10. Barsukov I.L., Lian L.-Y., Ellis J., Sze K.-H., Shaw W.V., Roberts G.C.K. J. Mol. Biol. 262:1996;543.
11. Wu W.-J., Anderson V.E., Raleigh D.P., Tonge P.J. Biochemistry. 36:1997;2211.
12. For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521.
13. For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521.
14. For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521.
15. For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521.
16. For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521.
17. For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521.
18. For reviews of X-ray structures of CoA-utilizing enzymes see: Engel, C.; Wierenga, R. Curr. Opin. Struct. Biol. 1996, 6, 790. Modis, Y.; Wierenga, R. Structure 1998, 6, 1345. For more recently reported structures see: Benning, M. M.; Wesenberg, G.; Liu, R.; Taylor, K. L.; Dunaway-Mariano, D.; Holden, H. M. J. Biol. Chem. 1998, 273, 33572. Wybenga-Groot, L. E.; Draker, K.; Wright, G. D.; Berghuis, A. M. Structure 1999, 7, 497. Hickman, A. B.; Namboodiri, M. A. A.; Klein, D. C.; Dyda, F. Cell 1999, 97, 361. Trievel, R. C.; Rojas, J. R.; Sterner, D. E.; Venkataramani, R. N.; Wang, L.; Zhou, J.; Allis, C. D.; Berger, S. L.; Marmorstein, R. Proc. Natl. Acad. Sci. USA 1999, 96, 8931. Clements, A.; Rojas, J. R.; Trievel, R. C.; Wang, L.; Berger, S. L.; Marmorstein, R. EMBO J. 1999, 18, 3521.
19. Lin Y., Fletcher C.M., Zhou J., Allis C.D., Wagner G. Nature. 400:1999;86.
20. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Wheeler, O. H.; de Rodriguez, E. E. G. J. Org. Chem. 1964, 29, 1227.
21. Allinger, N. L.; Zalkow, V. J. Org. Chem. 1960, 25, 701. Wheeler, O. H.; de Rodriguez, E. E. G. J. Org. Chem. 1964, 29, 1227.
22. Kirby A.J. Adv. Phys. Org. Chem. 17:1980;183.
23. Airapetyan, G. M.; Zherebchenko, P. G.; Bystrova, V. M.; Benevolenskaya, Z. V.; Kuleshova, N. D.; Linkova, M. G.; Kildisheva, O. V.; Knunyants, I. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1967, 317.
24. Howson W., Kitteringham J., Mistry J., Mitchell M.B., Novelli R., Slater R.A., Swayne G.T.G. J. Med. Chem. 31:1988;352.
25. Knouzi, M.; Vaultier, M.; Carrie, R. Bull. Soc. Chim. Fr. 1985, 815.
26. Oiry J., Pue J.Y., Imbach J.L., Fatome M., Sentenac-Roumanou H., Lion C. J. Med. Chem. 29:1986;2217.
27. Dauben W.G., Hendricks R.T., Pandy B., Wu S.C., Zhang X., Luzzio M.J. Tetrahedron Lett. 44:1995;519.
28. Shemin, D., Ed. Biochemical Preparations; John Wiley & Sons: New York, 1957; Vol. 5, p 1.
29. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M. Tetrahedron Lett. 1977, 155.
30. O'Brien W.E. Anal. Biochem. 76:1976;423.
31. Martin D.P., Drueckhammer D.G. Biochem. Biophys. Res. Commun. 192:1993;1155.
32. Martin D.P., Bibart R.T., Drueckhammer D.G. J. Am. Chem. Soc. 116:1994;4660.
33. Hirschbein B.L., Mazenod G.M., Whitesides G.M. J. Org. Chem. 47:1982;3765.
34. Mohamadi F., Richards N.G.J., Guida W.C., Kiskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440.
35. Pachler K.G.R. Spectrochim. Acta. 20:1964;581.
36. Teller, J. H.; Powers, S. G.; Snell, E. E. J. Biol. Chem. 1976, 251, 3780. Aberhart, D. J. J. Am. Chem. Soc. 1979, 101, 1354.
37. Teller, J. H.; Powers, S. G.; Snell, E. E. J. Biol. Chem. 1976, 251, 3780. Aberhart, D. J. J. Am. Chem. Soc. 1979, 101, 1354.
38. Epelbaum S., LaRossa R.A., VanDyk T.K., Elkayam T., Chipman D.M., Barak Z. J. Bacteriol. 180:1998;4056.
39. Ketopantoate hydroxymethyltransferase, the enzyme that catalyzes the addition of the hydroxymethyl group to 11, has been shown to accept α-ketobutyrate but not pyruvate as a substrate; Powers, S. G.; Snell, E. E. J. Biol. Chem. 1976, 251, 3786.
40. Miller S.L., Schlesinger G. J. Mol. Evol. 36:1993;308.
41. Bruice, T. C.; Pandit, K. P. J. Am. Chem. Soc. 1960, 82, 5858. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1997, 119, 9103.
42. Bruice, T. C.; Pandit, K. P. J. Am. Chem. Soc. 1960, 82, 5858. Lightstone, F. C.; Bruice, T. C. J. Am. Chem. Soc. 1997, 119, 9103.
43. Bibart R.T., Vogel K.W., Drueckhammer D.G. J. Org. Chem. 64:1999;2903.
44. Mieyal J.J., Webster L.T., Siddiqui U.A. J. Biol. Chem. 249:1974;2633.
45. Kunttu H., Raaska T., Rasanen M. Theochem. 184:1989;277.
46. Wu D., Tian A., Sun H. J. Phys. Chem. 102:1998;9901.
47. Pauling, L. Festschr. Prof. Dr. Arthur Stoll Siebzigsten Geburstag 1958, 597.
48. Fersht A.R., Shindler J.S., Tsui W.-C. Biochemistry. 19:1980;5520.
49. Izard T., Geerlof A. EMBO J. 18:1999;2021.