Mechanism of dimethylallyltryptophan synthase: Evidence for a dimethylallyl cation intermediate in an aromatic prenyltransferase reaction

Journal of the American Chemical Society

Volumn 131, Issue 39, 2009, Pages 13932-13933

  Luk, Louis Y P ^a   Tanner, Martin E ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATIVE MECHANISMS; CARBOCATIONS; CATION INTERMEDIATES; CHEMICAL EQUATIONS; DIPHOSPHATES; DISSOCIATIVE MECHANISMS; ELECTROPHILIC AROMATIC SUBSTITUTIONS; ENZYMATIC REACTION; ERGOT ALKALOIDS; INDOLE RINGS; ION PAIRS; ISOTOPE EXCHANGE; KINETIC ISOTOPE EFFECTS; L-TRYPTOPHAN; PRENYLTRANSFERASE; SINGLE-STEP; STARTING MATERIALS; SYNTHASE REACTIONS; SYNTHASES;

AMINO ACIDS; AROMATIC COMPOUNDS; BIOCHEMISTRY; DISSOCIATION; ISOTOPES; LABELS; PHOSPHORUS; POSITIVE IONS; SUBSTITUTION REACTIONS;

ENZYMES;

DIMETHYLALLYLTRANSFERASE; DIMETHYLALLYLTRYPTOPHAN SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENZYME MECHANISM; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

ALKYL AND ARYL TRANSFERASES; ALLYL COMPOUNDS; DIMETHYLALLYLTRANSTRANSFERASE; HEMITERPENES; MODELS, CHEMICAL; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; ORGANOPHOSPHORUS COMPOUNDS;

EID: 70349620845     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906485u     Document Type: Article

References (32)

1. (a) Steffan, N.; Unsöld, I. A.; Li, S.-M. ChemBioChem 2007, 8, 1298-1307.
2. (b) Gebler, J. C.; Woodside, A. B.; Poulter, C. D. J. Am. Chem. Soc. 1992, 114, 7354-7360.
3. (c) Shibuya, M.; Chou, H.-M.; Fountoulakis, M.; Hassam, S.; Kim, S.-U.; Kobayashi, K.; Otsuka, H.; Rogalska, E.; Cassady, J. M.; Floss, H. G. J. Am. Chem. Soc. 1990, 112, 297-304.
4. (a) Ding, Y.; Williams, R. M.; Sherman, D. H. J. Biol. Chem. 2008, 283, 16068-16076.
5. (b) Unsöld, I. A.; Li, S.-M. Microbiology 2005, 151, 1499-1505.
6. (c) Tsai, H.-F.; Wang, H.; Gebler, J. C.; Poulter, C. D.; Schardl, C. L. Biochem. Biophys. Res. Commun. 1995, 216, 119-125.
7. Liang, P.-H.; Ko, T.-P.; Wang, A. H.-J. Eur. J. Biochem. 2002, 269, 3339-3354.
8. (a) Lu, Y.-P.; Liu, H.-G.; Liang, P.-H. Biochem. Biophys. Res. Commun. 2009, 379, 351-355.
9. (b) Kellogg, B. A.; Poulter, C. D. Curr. Opin. Chem. Biol. 1997, 1, 570-578.
10. (c) Poulter, C. D.; Wiggins, P. L.; Le, A. T. J. Am. Chem. Soc. 1981, 103, 3296-3927.
11. (d) Christianson, D. W. Chem. Rev. 2006, 106, 3412-3442.
12. (e) Cane, D. E. Chem. Rev. 1990, 90, 1089-1103.
13. (a) Huang, C.-C.; Hightower, K. E.; Fierke, C. A. Biochemistry 2000, 39, 2593-2602.
14. (b) Weller, V. A.; Distefano, M. D. J. Am. Chem. Soc. 1998, 120, 7975-7976.
15. (a) Heide, L. Curr. Opin. Chem. Biol. 2009, 13, 171-179.
16. (b) Tello, M.; Kuzuyama, T.; Heide, L.; Noel, J. P.; Richard, S. B. Cell. Mol. Life Sci. 2008, 65, 1459-1463.
17. Lakhdar, S.; Westermaier, M.; Terrier, F.; Goumont, R.; Boubaker, T.; Ofial, A. R.; Mayr, H. J. Org. Chem. 2006, 71, 9088-9095.
18. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1383-1396.
19. (a) Mullins, L. S.; Raushel, F. M. Methods Enzymol. 1995, 249, 398-425.
20. (b) Raushel, F. M.; Villafranca, J. J. CRC Crit. Rev. Biochem. 1988, 23, 1-26.
21. (a) Singh, A. N.; Hester, L. S.; Raushel, F. M. J. Biol. Chem. 1987, 262, 2554-2557.
22. (b) Cohn, M.; Hu, A. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 200-203.
23. The relative rate of the PIX reaction to net product formation (partitioning ratio) was approximately 0.26 (see Supporting Information).
24. (a) Cane, D. E.; Chiu, H.-T.; Liang, P.-H.; Anderson, K. S. Biochemistry 1997, 36, 8332-8339.
25. (b) Kirsch, J. F. Secondary Kinetic Isotope Effects. In Isotope Effects on Enzyme-catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, MD, 1977; pp 100-121.
26. (a) Zollinger, H. Adv. Phys. Org. Chem. 1964, 2, 163-199.
27. (b) Melander, L. Isotope Effects on Reaction Rates; Ronald Press: New York, 1960; pp 107-122.
28. (a) Luk, L. Y. P.; Bunn, S.; Liscombe, D. K.; Facchini, P. J.; Tanner, M. E. Biochemistry 2008, 47, 3272-3282.
29. (b) Maresh, J. J.; Giddings, L. A.; Friedrich, A.; Loris, E. A.; Panjikar, S.; Trout, B. L.; Stockigt, J.; Peters, B.; O'Connor, S. E. J. Am. Chem. Soc. 2008, 130, 710-723.
30. (a) Croteau, R. B.; Shaskus, J. J.; Renstrom, B.; Felton, N. M.; Cane, D. E.; Saito, A.; Chang, C. Biochemistry 1985, 24, 7077-7085.
31. (b) Mash, E. A.; Gurria, G. M.; Poulter, C. D. J. Am. Chem. Soc. 1981, 103, 3927-3929.
32. Cane, D. E.; Iyengar, R. J. Am. Chem. Soc. 1979, 101, 3385-3388.