Catalysis by desolvation: The catalytic prowess of SAM-dependent halide-alkylating enzymes

Journal of the American Chemical Society

Volumn 135, Issue 39, 2013, Pages 14473-14475

  Lohman, Danielle C ^a,b   Edwards, David R ^a,c   Wolfenden, Richard ^a  

^a UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c AFTON CHEMICAL CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID-BASE CATALYSIS; ALKYL HALIDES; BIOLOGICAL FIXATION; ELEVATED TEMPERATURE; HALIDE IONS; RATE ENHANCEMENT; S-ADENOSYLMETHIONINE; SECOND-ORDER RATE CONSTANTS;

CATALYSIS; METAL IONS; RATE CONSTANTS;

ENZYMES;

HALIDE; METAL ION; S ADENOSYLMETHIONINE; WATER;

ALKYLATION; ARTICLE; CATALYST; CONTROLLED STUDY; DECOMPOSITION; ENZYME MECHANISM; NUCLEOPHILICITY; TEMPERATURE;

ALKYLATION; ANIONS; BACTERIAL PROTEINS; HALOGENS; MICROMONOSPORACEAE; OXIDOREDUCTASES; S-ADENOSYLMETHIONINE; STREPTOMYCES; WATER;

EID: 84885119375     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja406381b     Document Type: Article

References (25)

1. O'Hagan, D.; Schaffrath, C.; Cobb, S. L.; Hamilton, J. T. G.; Murphy, C. D. Nature 2004, 427, 561
2. Eustáquio, A. S.; Pojer, F.; Noel, J. P.; Moore, B. S. Nat. Chem. Biol. 2008, 4, 69
3. Schmidberger, J. W.; James, A. B.; Edwards, R.; Naismith, J. H.; O'Hagan, D. Angew. Chem., Int. Ed. 2010, 49, 3646
4. II cofactors to conduct oxidative halogenation of their substrates in the biosynthesis of a variety of natural products: Vaillancourt, F. H.; Yin, J.; Walsh, C. T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 1011 and references cited therein)
5. Hoffman, J. L. Biochemistry 1986, 25, 1444
6. Iwig, D. F.; Booker, S. J. Biochemistry 2004, 43, 3496
7. Glew, D. N.; Moelwyn-Hughes, E. A. Proc. R. Soc. Lond. A 1952, 211, 254
8. Senn, H. M.; O'Hagan, D.; Thiel, W. J. Am. Chem. Soc. 2005, 127, 13643
9. Zhu, X. F.; Robinson, D. A.; McEwan, A. R.; O'Hagan, D.; Naismith, J. H. J. Am. Chem. Soc. 2007, 129, 14597
10. Deng, H.; McMahon, S. A.; Eustáquio, A. S.; Moore, B. S.; Naismith, J. H.; O'Hagan, D. ChemBioChem 2009, 10, 2455
11. Pearson, R. G.; Sobel, H.; Songstad, J. J. Am. Chem. Soc. 1968, 90, 319
12. Swain, C. G. S.; Scott, C. B. J. Am. Chem. Soc. 1953, 75, 246
13. Pocker, Y.; Parker, A. J. J. Org. Chem. 1966, 31, 1526
14. Cadicamo, C. D.; Courtieu, J.; Deng, H.; Meddour, A.; O'Hagan, D. ChemBioChem 2004, 5, 685
15. Eustáquio, A. S.; Harle, J.; Noel, J. P.; Moore, B. S. ChemBioChem 2008, 9, 2215
16. Dzingeleski, G. D.; Wolfenden, R. Biochemistry 1993, 32, 9143
17. 16-fold at 37 C: Mihel, I.; Knipe, J. O.; Coward, J. K.; Schowen, R. L. J. Am. Chem. Soc. 1979, 101, 4349
18. Stockbridge, R. B.; Wolfenden, R. J. Biol. Chem. 2009, 284, 22747
19. Schroeder, G. K.; Wolfenden, R. Biochemistry 2007, 46, 4037
20. Hughes, E. D. I.; Ingold, C. K. J. Chem. Soc. 1935, 244
21. Vincent, M. A.; Hillier, I. H. Chem. Commun. 2005, 5902
22. Swain, C. G. B.; Burrows, W. D.; Schowen, B. J. J. Org. Chem. 1968, 33, 2534
23. Swain, C. G. K.; Kaiser, L. E. J. Am. Chem. Soc. 1958, 80, 4089
24. Stockbridge, R. B.; Wolfenden, R. Chem. Commun. 2010, 46, 4306
25. For a lucid review of these issues: Schowen, R. L. Transition States of Biological Processes; Fandour, R. D.; Schowen, R. L., Eds.; Plenum Press: New York, 1978; pp 77-114.